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1 Vol. 9, o. 6 lefin Metathesis Features include: First Generation Grubbs Catalyst
2 2 Introduction Introduction Yves Chauvin obert. Grubbs ichard. Schrock erisson Chauvin 1971 Figure 2 1 Katz Schrock Grubbs Grubbs 5 CM CAMCM EM M CM ADMET [M] [M] William Sommer roduct Manager [M] eferences: (1) (a) Schrodi, Y.; ederson,. L. Aldrichimica Acta 2007, 40, 45. (b) Adv. Synth. Catal. 2007, 349, (lefi n Metathesis Special Issue). (c) Grubbs,.. Tetrahedron 2004, 60, (d) andbook of Metathesis; Grubbs,.., Ed.; Wiley-VC: Weinheim, 2003; Vols (e) Trnka, T. M.; Grubbs,.. Acc. Chem. es. 2001, 34, 18. (f ) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, (g) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. 1997, 36, (2) (a) erission, J. L.; Chauvin, Y. Makromol. Chem. 1971, 141, 161. (b) Chauvin, Y. Angew. Chem., Int. Ed. 2006, 45, (3) Katz T. J.; othchild,. J. Am. Chem. Soc. 1976, 98, (4) Schrock,.. et al. J. Am. Chem. Soc. 1990, 112, (5) guyen, S. T. et al. J. Am. Chem. Soc. 1992, 114, Figure 1 [M] Grubbs - M ADMET CM CM CAS MSDS sigma-aldrich.com/japan M, I aman, UV DF My rofile 1) Web language=japanese, 2) MSDS=English, 3) Country=Japan 3 Submit Web Tel: Fax: sialjpts@sial.com
3 3 The Grubbs Catalysts Cy 3 Cy 3 Cy Grubbs 1 st generation catalyst Grubbs 2 nd generation catalyst Grubbs 3 rd generation catalyst Cy oveyda-grubbs 1 st generation catalyst oveyda-grubbs 2 nd generation catalyst Cy 3 Cy + 3 -BF iers-grubbs 1 st generation catalyst The Grubbs Catalysts Cy + 3 -BF 4 Cy 3 Cy 3 Cy iers-grubbs 2 nd generation catalyst Cy Discover ew Cross-Coupling Catalysts 2 d i-r Cy2 2 d Cy2 2 d i-r Cy2 i-r 2 d t-bu 2 i-r i-r i-r i-r i-r (from Xos) (from Sos) (from os) (from t-buxos) For more information, visit sigma-aldrich.com/buchwald sigma-aldrich.com Tel: Fax: safcjp@sial.com
4 4 ing-osing Metathesis ing-osing Metathesis C-C Villemin Grubbs 3 Grubbs Scheme 1 4 CM CM 2004 Wood Wood Scheme 2 2 mol Grubbs 25 mol Grubbs-oveyda 76 Grubbs oveyda-grubbs Grubbs iers iers Grubbs 0 Grubbs Scheme Grubbs 35 iers 50 M Scheme 4 7 IV Scheme 1 Scheme 2 Scheme 3 Et MB 76% Et Cy 3 Cy3 Cy 3 X (2-4 mol %) C66, 20 C X =, C 1-2 h 93% CF 3 X TBS 89% 85% Cy3 Cy3 (2 mol %) 2C=C2 C22, 25 C (25 mol %) toluene, Δ Cy3 BF4 (1 mol %) CD22, 0 C, 2h ingenol Et 98% Et >90% conversion 25% completion with Grubbs Catalyst (2 nd Generation) MB C C2 B(C 6F 5) 4 sigma-aldrich.com/japan Scheme 4 Tel: Fax: sialjpts@sial.com
5 5 Stoltz Grubbs oveyda-grubbs CM Scheme 5 8 i-bu (5 mol %) benzene, 60 C i-bu 97% (+)-elatol = 22β - CM CM oveyda-grubbs Scheme 6 Donohoe CM oveyda-grubbs Grubbs TS TFA Scheme 7 Scheme (10 mol %) 1 toluene, 80 C 1 = TBS, 2 = Me, ; all combinations with 22α- and 22β- 1 =, 2 = Me, ; all combinations with 22α- and 22β- Scheme % ing-osing Metathesis Z - - Z - CM Grubbs 2 CM 72 Scheme 8 11 Et (10 mol %) toluene, 60 C then 1 eq TS 60% 3 C n-bu Cy 3 (10 mol %) toluene, reflux then 0.6 eq TFA 38% Scheme 7 Tel: Fax: safcjp@sial.com
6 6 ing-osing Metathesis CAM Schrock C-C Fürstner 14 CAM Scheme 9 eferences: (1) icolaou, K. C. et al. Angew. Chem., Int. Ed. 2005, 44, (2) (a) Villemin, D. Tetrahedron Lett. 1980, 21, (b) Tsuji, J. et al. Tetrahedron Lett. 1980, 21, (3) Fu, G. C. et al. J. Am. Chem. Soc. 1993, 115, (4) Fu, G. C. et al. J. Am. Chem. Soc. 1993, 115, (5) ickel, A. et al. J. Am. Chem. Soc. 2004, 126, (6) omero,. E. et al. Angew. Chem. Int. Ed. 2004, 43, (7) omero,. E. iers, W. E. J. Am. Chem. Soc. 2005, 127, (8) White, D. E. et al. J. Am. Chem. Soc. 2008, 130, 810. (9) Matsuya, Y. et al. rg. Lett. 2009, 11, (10) (a) Donohoe, T. J. et al. Eur. J. rg. Chem. 2005, (b) Donohoe, T. J. et al. Tetrahedron 2008, 64, 809. (c) Donohoe, T. J. et al. rg. Lett. 2006, 8, 543. (d) Donohoe, T. J. et al. Chem. Eur. J. 2008, 14, (11) Donohoe, T. J. et al. Angew. Chem. Int. Ed. 2008, 47, (12) Schrock,.. Chem. ev. 2002, 102, 145. (13) (a)fürstner, A. et al. Chem. Commun. 2005, (b) Schrock,.. et al. Adv. Synth. Catal. 2007, 349, 55. (14) Bindl, M. et al. J. Am. Chem. Soc. 2009, 131, Me TIS Et TS Et Et Me TIS Cy3 (7.5 mol %) C22, Δ Et TIS then TS TIS (85% yield over two steps) Me Me C2Me C 2Me Cy3 (15 mol %) toluene, Δ 72% ( )-(Z)-deoxypukalide Scheme 8 3Si Mo Si3 3Si (20 mol %) sigma-aldrich.com/japan Scheme 9 87% 54% Tel: Fax: sialjpts@sial.com
7 7 Cross Metathesis Corey 3 Scheme 1 Cy3 Cy3 (10 mol %) C2C2, rt Me Me Me Me Cross Metathesis Grubbs o- - oveyda-grubbs 4 Scheme 2 Grubbs oveyda-grubbs 5 mol Grubbs owell β - α- -β - oveyda- Grubbs Grubbs 5 Scheme 3 6 Botta β Grubbs CuS Scheme 4 7 eferences: (1) Connon, S. J. et al. Angew. Chem. Int. Ed. 2003, 42, (2) Chatterjee, A. K. et al. J. Am. Chem. Soc. 2003, 125, (3) (a) Xiong, Z. et al. J. Am. Chem. Soc. 2000, 122, (b) Xiong, Z. et al. J. Am. Chem. Soc. 2000, 122, (4) Stewart, I. C. et al. rg. Lett. 2008, 10, 441. (5) Liang, Y.et al. Tetrahedron Lett. 2009, 50, (6) Diver, S. T. et al. Chem. ev. 2004, 104, (7) Castagnolo, D. et al. J. rg. Chem. 2009, 74, Scheme 1 Et Et Ac 89%, >20:1 dr Scheme 2 + Scheme Et Et (5 mol %) C22, Δ 91%, >20:1 dr Et (3 x 2 mol %) C22, Δ Cy3 (10 mol %) 2 eq. CuS 4 t-bu/2 1:1 μw, 80 C then, I 2 Bz Et Bz 98%, >20:1 dr MB Et 66%, 3:2 dr 85% E:Z = 1:1 Bz 51% 68% 39% 63% Scheme 4 Tel: Fax: safcjp@sial.com
8 8 ing-pening Metathesis olymerization M ing-pening Metathesis olymerization M M Ziegler atta M Grubbs M 2 M M M Grubbs Synthesis of ush-like olymers via M Cheng M - Cheng Grubbs DI Scheme 1 3 eferences: (1) (a) Ziegler,. et al. Angew. Chem. 1955, 67, 541.(b) atta, G. Angew. Chem. 1956, 68, 393. (2) guyen, S. T. et al. J. Am. Chem. Soc. 1992, 114, (3) Lu,. et al. J. Am. Chem. Soc., 2009, 131, TMS 1.0 eq Scheme eq (5 mol %) x TMS n brush-like polymer TF: C22 (9:1) y TMS x y polymerization of amino acid -carboxyanhydride CMU sigma-aldrich.com/japan + C F6 - For more information, visit sigma-aldrich.com/comu sigma-aldrich.com ATU Tel: Fax: Ethyl(hydroxyimino)cyanoacetate (XYMA) Bt, At C At sialjpts@sial.com
9 9 Catalysts andbook of Metathesis, 3 volume set ISB Z EA 1 ea 69,600 2,6-Diiso pro pyl phenyl imido-neoph yl idene[( S )-( )-BIE] molybdenum(vi), 97.0% (C) [ ] C Mo 2 FW purum, ring-closing metathesis catalyst 3C 3C 3C 3C i-r t-bu Mo t-bu i-r C3 C MG-F 100 mg 53,500 Tris(triphenylsilyloxy)molybdenum nitride pyridine complex, 95% C Mo 2 3 Si 3 FW contains up to 10 wt. % toluene Si Mo Si Si mg 18,000 oveyda-grubbs Catalyst 1 st Generation [ ] C FW ,111,121 sigma-aldrich.com/materialicense MG 100 mg 10, MG 500 mg 41, G 2 g 124,100 Dichloro(3-methyl-2-butenylidene)bis(tricyclohexylphosphine) ruthenium(ii) [ ] C FW C C 3 C3 C3 Catalysts Grubbs Catalyst, 2 nd Generation [ ] C FW C 3C C3 C3 3C 6,111,121 7,329,758 sigma-aldrich.com/materialicense sialjpts@sial.com Materia MG 100 mg 12, MG 500 mg 40, G 2 g 112,100 oveyda-grubbs Catalyst 2 nd Generation [ ] C FW C 3C C3 C3 3C 6,921,735 sigma-aldrich.com/materialicense MG 100 mg 13, MG 500 mg 54, G 2 g 159,000 3C C3 C3 C3 5,969,170 sigma-aldrich.com/materialicense G 1 g 21, G 5 g 74,500 Dichloro(3-methyl-2-butenylidene)bis(tricyclopentylphosphine) ruthenium(ii) [ ] C FW ,969,170 sigma-aldrich.com/materialicense G 1 g 21, G 5 g 69,700 Grubbs Catalyst, 1 st generation [ ] C FW C 3 C3 6,111,121 sigma-aldrich.com/materialicense G 1 g 20, G 5 g 74,000 Tel: Fax: safcjp@sial.com
10 10 [1,3-Bis(2-methylphenyl)-2-imidazolidinylidene]dichloro- (benzylidene) (tricyclohexylphosphine)ruthenium(ii) [ C FW C3 C3 [1,3-Bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene]dichloro- [3-(2-pyridinyl-κ )propylidene-κc]ruthenium(ii) [ ] 3C C3 C C C FW C C3 Catalysts 6,111,121 7,329,758 sigma-aldrich.com/materialicense sialjpts@sial.com Materia MG 100 mg 11, MG 500 mg 42, G 2 g 137,400 [1,3-Bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene] dichloro(benzylidene)bis(3-bromopyridine)ruthenium(ii) C C FW C C 3 3C C3 C 3 11/094,102 sigma-aldrich.com/materialicense MG 100 mg 11, MG 500 mg 44, G 2 g 135,500 the nium Metathesis Catalysts Kit I sigma-aldrich. com/materialicense sialjpts@sial.com Materia info@materia-inc.com 6,759,537 sigma-aldrich.com/materialicense MG 100 mg 10, MG 500 mg 43, G 2 g 130,800 [1,3-Bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene]dichloro- (3-methyl-2-butenylidene) (tricyclohexylphosphine)ruthenium(ii) C C C3 FW C C 3 3C 5,969,170 7,529,758 sigma-aldrich.com/materialicense sialjpts@sial.com Materia MG 100 mg 8, MG 500 mg 31, G 2 g 98,700 C 3 C3 C 3 thenium Metathesis Catalysts Kit I Components Grubbs Catalyst, 1 st Generation (Aldrich ) 1 G Grubbs Catalyst, 2 nd Generation (Aldrich ) 100 MG oveyda-grubbs Catalyst 2 nd Generation (Aldrich ) 100 MG oveyda-grubbs Catalyst 1 st Generation (Aldrich ) 100 MG Dichloro(3-methyl-2-butenylidene)bis(tricyclohexylphosphine)ruthenium(II) (Aldrich ) 1 G Dichloro(3-methyl-2-butenylidene)bis(tricyclopentylphosphine)ruthenium(II) (Aldrich ) 1 G [1,3-Bis(2-methylphenyl)-2-imidazolidinylidene]dichloro(benzylidene) (tricyclohexylphosphine)ruthenium(ii) (Aldrich ) 100 MG [1,3-Bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene]dichloro(benzylidene)bis(3- bromopyridine)ruthenium(ii) (Aldrich ) 100 MG [1,3-Bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene]dichloro(3-methyl-2- butenylidene) (tricyclohexylphosphine)ruthenium(ii) (Aldrich ) 100 MG [1,3-Bis(2-methylphenyl)-2-imidazolidinylidene]dichloro(2- isopropoxyphenylmethylene)ruthenium(ii) (Aldrich ) 100 MG [1,3-Bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene]dichloro[3-(2-pyridinyl-κ ) propylidene-κ C ]ruthenium(ii) (Aldrich ) 100 MG KT 1 kit 133,800 sigma-aldrich.com/japan [1,3-Bis(2-methylphenyl)-2-imidazolidinylidene]dichloro- (2-isopropoxyphenylmethylene)ruthenium(II) C FW C3 Tel: Fax: C 3 6,921,735 sigma-aldrich.com/materialicense MG 100 mg 11, MG 500 mg 44, G 2 g 135,500 3C C3 sialjpts@sial.com
11 11 Dichloro(tricyclohexylphosphine)[(tricyclohexylphosphoranyl)- methylidene]ruthenium tetrafluoroborate, 95% C B 2 F 4 2 FW BF4 - [1,3-Bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene]dichloro- [(tricyclohexylphosphoranyl)methylidene]ruthenium tetrafluoroborate, 95% [ ] C 40 60B 2F4 2 FW C C3 3C C 3 C3 3C F F B F F UTI artnership 7,354,140 Materia sigma-aldrich.com/materialicense sialjpts@sial.com Materia info@ materia-inc.com MG 100 mg 6, MG 500 mg 26, G 2 g 79,000 UTI artnership 7,354,140 Materia sigma-aldrich.com/materialicense sialjpts@sial.com Materia info@ materia-inc.com MG 100 mg 11, MG 500 mg 43, G 2 g 130,000 Catalysts TurboGrignards for al/mg Exchange of Aryl and eteroaryl Compounds Knochel-auser-Base for Selective Deprotonations FG Mg Li = Mg Li (TurboGrignard) FG = alkyl, alkenyl, ', C 2 ', C, 2, halogen C 3 3 C Mg Li FG Mg Li Mg Li 3 C 3 C C 3 C 3 Mg Li TF Sold in partnership with Selective 1,2-Additions La 3 /Li TF For more information, visit sigma-aldrich.com/metalations sigma-aldrich.com Tel: Fax: safcjp@sial.com
12 Chem roduct Central Substructure Search Building Blocks rganic Building Blocks eterocyclic Building Blocks Amino Acid Derivatives Unnatural Amino Acid Derivatives Monosaccharides ucleosides Chiral Building Blocks rganometallic eagents Boronic Acids and Derivatives Grignard eagents ieke and rganozinc eagents rganolithium rganosilicon rganotin rganoaluminum thers Synthetic eagents Coupling Lewis Acids C-C Bond Formation rganic Acids C-X Bond Formation (alogen) Inorganic Acids C-X Bond Formation (onhalogen) osphazene Bases rganic Bases xidation Inorganic Bases eduction Inorganic Salts rotection and Derivatization Dehydrating eagents adical Chemistry Compressed and ase Transfer Catalysts Liquified Gases Chelation/Complexation Compounds Asymmetric Synthesis Chiral Catalysts, Ligands, and eagents Chiral Auxiliaries Chiral Building Blocks Chiral esolution eagents Ionic Liquids Ammonium Choline Imidazolium osphonium yrazolium yridinium yrrolidinium Sulfonium Specialty Synthesis igh Throughput Synthesis Chemical Ligation eptide Synthesis Carbohydrate Synthesis ligonucleotide Synthesis Enzyme-Mediated Synthesis Fluorous Synthesis Supported Synthesis
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Vol. 9, o. 5 Gold Chemistry Features include: Gold complex used in various transformations with alkynes and alkenes 2 Introduction Introduction 20 1973 Bond 1 C 2 utchings 3 10 4 ashmi Echavarren olan
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Precisely Designed Catalysts News Letter Vol. 5 May, 2016
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寄稿論文 ボロンアルドール反応の新展開 | 東京化成工業
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1 効率的な不斉触媒反応を可能に する新しい C 配位子の開発 関西大学化学生命工学部化学 物質工学科 准教授坂口聡 新型インフルエンザ治療薬 タミフル オセルタミビルリン酸塩 ロッシュ社による製造法 シキミ酸 Ms Et Et V. Farina, J. D. Brown, Angew. Chem., Int. Ed. 2006, 45, 7330. 2 タミフルの新合成法 + C 2 C 2 CF
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MCM-41 M41 MCM-41 M41 2 3 m 2 /g nm nm Mn Ti Ti H N 2 S Ti-MCM-41, H H N H H 2 2 -Urea, CH 2 Cl 2, H 2 S + S 1b 2b 3b 54%, 58% ee Ti M41 H 2 As 4 ZP 4 ZP ZS ZS 5 Me Me Me Me M41 / 15 mg MeH 1.0 mmol 89%
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寄稿論文 新光延試薬 | 東京化成工業
DEAD TPP A Et C C Et Et C C Et 2 A A ex. ucleophiles (A) P 3 P 3 1 xygen itrogen Carbon Sulfur C 3 S Ts Tf Scheme 1. TPP DEAD TPP DEAD redox condensation Walden Bz Tf DEAD-TPP 87% Tf Bz Scheme 2. pk a
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th 37 ICh Theoretical Examination - - - - 5 - - : - ( ): ( ) - : 279 - - - - - - - G D L U C K 1 2 1 amu = 1.6605 10-27 kg N = 6.02 10 23 mol -1 k = 1.3806503 10-23 J K -1 e = 1.6022 10-19 C F = 9.6485
2 Introduction Dudley 4-2- SES SES-Cl SES- 2 SES 2 Aldrichimica Acta ALDIC WELCMES TE 37T GLM T MILWAUKEE Acta Aldrichimica Acta 40 Aldrichimica Acta
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Scheme 1 Scheme 2 Chart 1 Scheme ( 44 )
Catalytic Asymmetric Aldol Reactions in Aqueous Media Tomoaki Hamada, Kei Manabe, and Shu Kobayashi* Catalytic asymmetric aldol reactions in aqueous media have been developed using Pr(OTf)3 and chiral
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上原記念生命科学財団研究報告集, 25 (2011) 6. 新規多点制御型有機分子触媒の創製を基盤とするドミノ型反応の開発 笹井宏明 Key words: 不斉有機分子触媒, イソインドリン, テトラヒドロピリジン, ドミノ反応, 二重活性化 大阪大学産業科学研究所機能物質科学研究分野 緒言連続する反応を一つの容器内で単一の操作で進行させるドミノ型反応は, 多段階反応における中間体の単離精製を必要とせず,
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