水素移動型不斉還元触媒｜関東化学株式会社
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1 99% yield, 96% ee (S/C = 1000) 89% yield, 99% ee (S/C = 300) >99% yield, 97% ee () X 78% yield, 95% ee () (S,S)-u cat X = C, 3, 2 = H, CH 3, F % yield, 92-98% ee (S/C = ) 100% yield dl:meso = 98.6:1.4, >99% ee (S/C = 1000) ( ) n 97% yield, 95% ee () = CH(CH 3 ) 2, n = 0, 94% yield, 75% ee = C 2H 5, n = 1, 94% yield, 93% ee = C 2H 5, n = 3, 99% yield, 95% ee >99% yield, 98% ee ()
2 Asymmetric Transfer Hydrogenation Catalysts Contents
3 EAT 10),13),14) 1) 12) 2- u ucl[(s,s)-tsdpen]( 6 -arene) u[(s,s)-tsdpen]( 6 -arene) Ts Ts n n H 2 u Cl H u Ts = S 2 C 6 H 4 -p-ch 3 1a ; n = 1-CH 3-4-CH(CH 3 ) 2 1b ; n = 1,3,5-(CH 3 ) 3 Ts = S 2 C 6 H 4 -p-ch 3 3a ; n = 1-CH 3-4-CH(CH 3 ) 2 3b ; n = 1,3,5-(CH 3 ) 3 1c ; n = 1,2,3,4,5,6-(CH 3 ) 6 ucl[(s,s)-msdpen]( 6 -arene) Ms u H 2 Cl n Ms = S 2 CH 3 2a ; n = 1-CH 3-4-CH(CH 3 ) 2 ucl(tsdpen)( 6 -arene) Cp hcl(tsdpen) Cp IrCl(Tsdpen) 1 1)-11) / 2
4 1), 3), 5) 7), 9) 2- (S,S)-cat + s + (CH 3 ) 2 CH 93 98% yield (S,S)-cat = [ucl 2 (mesitylene)] 2 (S,S)-TsDPE K( 1:2:5 = CH 3 97% ee = C 2 H 5 97% ee = m-cl 98% ee = p -Cl 93% ee = m-ch 3 96% ee 93% ee 98% ee 2), 3), 5) (S,S)-1b HC/(C 2 H 5 ) 3 28 s 93 99% yield S/C = % ee = m-cl 97% ee = p -Cl 95% ee = m-ch 3 98% ee = p -CH 3 97% ee 97% ee 83% ee 96% ee = CH 2 99% ee = (CH 2 ) 2 99% ee 70% yield, 83% ee 3
5 97% ee 95% ee carbonic anhydrase inhibitor MK ,2- - 1,2-2 s s s S X cat : (S,S)-3b >99%, 97% ee 4) cat : (S,S)-1b >99%, 98% ee 2), 3), 5) cat : (S,S)-1b 47%, 98% ee 2), 3), 5) cat : (,)-1b X = S 95%, 99% ee X = S 2 95%, 98% ee 2), 3), 5) C 2 CH 3 n C 2 H 5 Cl >97%, 95% ee 6) n = 1 94%, 93% ee 5) n = 3 99%, 95% ee 2) cat : (,)-1b 68%, 92% ee 2), 3), 5) X S/C = 300 (10 ) 89%, 99% ee 7) (40 ) 78%, 95% ee 7) 8) X : C, 3, 2 S/C = 100 (30 ) = H ; X = C 100%, 98%ee = H ; X = 3 65%, 92%ee = H ; X = 2 90%, 98%ee = F ; X = 2 95%, 96%ee = CH 3 ; X = 2 67%, 95%ee 4
6 2 12) / S/C = (S,S)-1a HC/(C 2 H 5 ) 3 DMF, = C 6 H 5 100%, dl:meso = 98.6:1.4, >99% ee = p-ch 3 -C 6 H 4 67%, dl:meso = 96.7:3.3, >99% ee = p-ch 3 -C 6 H 4 75%, dl:meso = 94.4:5.6, >99% ee = p-f-c 6 H 4 100%, dl:meso = 94.2:5.8, >99% ee 3 2 5), 13) 2- chokol G 14) -pentenomycin 15) racemic + (S,S)-cat CH 3 CCH unreacted alchol substrate catalyst time, h recovery, % ee, % config. k f /k s = H 3a >80 = p-ch 3 3a >30 = p-(ch 3 ) 2 3b >30 = CH 2 3a >40 = (CH 2 ) 2 3a >50 S/C = 500 5
7 4 5), 16), 17) (S,S)- or (,)-cat HC/(C 2 H 5 ) 3 solvent, H CH 3 H CH 3 S/C = %, 94% ee ( ) H H = CH 3 86%, 97% ee ( ) = C 6 H 5 83%, 96% ee ( ) H cat : ucl[(s,s)-s 2 dpen]( 6 -benzene) = 1-naphthyl S/C = %, 89% ee (S ) H H cat : ucl[(s,s)-s 2 dpen]( 6 -benzene) = 1-naphthyl 72%, 77% ee (S ) S X cat : ucl[(s,s)-s 2 dpen]( 6 -benzene) = 1-naphthyl X = S 82%, 85% ee (S ) X = S 2 84%, 88% ee (S ) 6
8 2) 12) 5.0 mmol ucl S,S -Tsdpen mesitylene 15.5 mg, mmol / ml 2 28 C ml, 136 mmol 8.7 ml, 230 mmol 11.0 g, 52.3 mol 5 ucl S,S -Tsdpen - p-cymene 33.3 mg, mmol 2 40 C 24 3, / 7
9 ) S. Hashiguchi, A. Fujii, J. Takehara, T. Ikariya,. oyori, Asymmetric Transfer Hydrogenation of omatic Ketones Catalyzed by Chiral uthenium(ii) Complexes, J. Am. Chem. Soc., 117, (1995) 2) A. Fujii, S. Hashiguchi,. Uematsu, T. Ikariya,. oyori, uthenium(ii)-catalyzed Asymmetric Transfer Hydrogenation of Ketones Using a Formic Acid-Triethylamine Mixture, J. Am. Chem. Soc., 118, (1996) 3),,,,, 54, (1996) 4) K. Matsumura, S. Hashiguchi, T. Ikariya,. oyori, Asymmetric Transfer Hydrogenation of, -Acetylenic Ketones, J. Am. Chem. Soc., 119, (1997) 5). oyori, S. Hashiguchi, Asymmetric Transfer Hydrogenation Catalyzed by Chiral uthenium Complexes, Acc. Chem. es., 30, (1997) 6) K. Kano, K. Murata, T. Ikariya, Stereoselective Synthesis of ptically active Pyridyl Alcohols via Asymmetric Transfer Hydrogenation of Pyridyl Ketons, Tetrahedron Lett., 41, (2000) 7) T. Koike, K. Murata, T. Ikariya, Stereoselective Synthesis of ptically Active -Hydroxy Ketones and anti-1,2-diols via Asymmetric Transfer Hydrogenation of Unsymmetrically Substituted 1,2-Diketones, rg. Lett., 2, (2000) 8) M. Watanabe, K. Murata, T. Ikariya, J. rg. Chem., in press. 9) M.J. Palmer, M. Wills, Asymmetric Transfer Hydrogenation of C= and C= Bonds, Tetrahedron Asymmetry, 10, (1999) 10) K.-J. Haack, S. Hashiguchi, A. Fujii, T. Ikariya,. oyori, The Catalyst Precursor, Catalyst, and Intermediate in the u II -Promoted Asymmetric HydrogenTransfer between Alcohols and Ketones, Angew. Chem. Int. Ed. Engl., 36, (1997) 11) M. Yamamoto, H. Ito, and. oyori, The Metal-Ligand Bifunctional Catalysis. A Theoretical Study on the uthenium(ii)-catalyzed Hydrogen Transfer Between Alcohols and Carbonyl Compounds, J. Am. Chem. Soc., 122, (2000) 12) K. Murata, K. kano, M. Miyagi, H. Iwane,. oyori, T. Ikariya, A Practical Stereoselective Synthesis of Chiral Hydrobenzoins via Asymmetric Transfer Hydrogenation of Benzils, rg.lett., 1, (1999) 13) S. Hashiguchi, A. Fujii, K.-J. Haack, K. Matsumura, T. Ikariya,. oyori, Kinetic esolution of acemic Secondary Alcohols by u II -Catalyzed Hydrogen Transfer, Angew. Chem. Int. Ed. Engl., 36, (1997) 14).M. Kanada, T. Taniguchi, K. gasawara, Asymmetric Hydrogenation Transfer Protocol for Enantiocontrolled Synthesis of (-)-Chokol G, Chem. Commun., 1998, ) Y. Iura, T. Sugahara, K. gasawara, xidative esolution of 2-Cyclopentenols By the Asymmetric Hydrogen Transfer Protocol, Tetrahedron Lett., 40, (1999) 16).Uematsu, A.Fujii, S.Hashiguchi, T.Ikariya,.oyori, Asymmetric Transfer Hydrogenation of Imines, J. Am. Chem. Soc., 118, (1996) 17),,,,, 55, (1997)
10 Cat.o. Chloro 1S, 2S -- p-toluenesulfonyl -1,2-diphenylethanediamine - p-cymene ruthenium ucl S,S -Tsdpen p-cymene S,S -1a Chloro 1, 2 -- p-toluenesulfonyl -1,2-diphenylethanediamine - p-cymene ruthenium ucl, -Tsdpen p-cymene, -1a Chloro 1S, 2S -- p-toluenesulfonyl -1,2-diphenylethanediamine - mesitylene ruthenium ucl S,S -Tsdpen mesitylene S,S -1b Chloro 1S, 2S -- p-toluenesulfonyl -1,2-diphenylethanediamine - mesitylene ruthenium ucl, -Tsdpen mesitylene, -1b Chloro 1S, 2S -- methanesulfonyl -1,2-diphenylethanediamine - p-cymene ruthenium ucl S,S -Msdpen p-cymene S,S -2a Chloro 1, 2 -- methanesulfonyl -1,2-diphenylethanediamine - p-cymene ruthenium ucl, -Msdpen p-cymene, -2a 1S, 2S -- p-toluenesulfonyl -1,2-diphenylethanediamine - p-cymene ruthenium u S,S -Tsdpen p-cymene S,S -3a 1, 2 -- p-toluenesulfonyl -1,2-diphenylethanediamine - p-cymene ruthenium u, -Tsdpen p-cymene, -3a 1S, 2S -- p-toluenesulfonyl -1,2-diphenylethanediamine - mesitylene ruthenium hydride uh S,S -Tsdpen mesitylene 1, 2 -- p-toluenesulfonyl -1,2-diphenylethanediamine - mesitylene ruthenium hydride uh, -Tsdpen mesitylene g 22, mg 7, g 22, mg 7, g 25, mg 8, g 25, mg 8, g 22, mg 7, g 22, mg 7, g 21, mg 6, g 21, mg 6, ucl S,S -Tsdpen p-cymene Lot o. substrate yield hydrobenzoin dl : meso optical purity benzil 100 % 97.8 : % ee, Conditions: S/C = 1000, HC 2 H/(C 2 H 5 ) 3 = 4.4/2.6, 40 C, 24h 9
11 Cat.o. 1S, 2S -- p-toluenesulfonyl -1,2-diphenylethanediamine S,S -TsDPE 99% ee ,000 HPLC g 13,000 1, 2 -- p-toluenesulfonyl -1,2-diphenylethanediamine, -TsDPE 1S, 2S -- Methanesulfonyl -1,2-diphenylethanediamine S,S -MsDPE 1, 2 - Methanesulfonyl -1,2-diphenylethanediamine, -MsDPE 99% ee g 40,000 HPLC g 13,000 99% ee g 35,000 HPLC g 10,000 99% ee g 35,000 HPLC g 10,000 Dichloro p-cymene ruthenim, dimer ucl 2 p-cymene 2 Cat.o g 70, % g 17, g 4,800 Cat.o g 44,000 1S, 2S - -1,2-Diphenyl-1,2-ethanediamine H 2 99% ee H 2 HPLC g 15, g 4,500 1, ,2-Diphenyl-1,2-ethanediamine H 2 H 2 99% ee HPLC g 44, g 15, g 5,000 S,S - -Hydrobenzoin 99% ee HPLC g 20, g 8,000, - -Hydrobenzoin 99% ee HPLC g 20, g 8,000 uthenium chloride n-hydrate ucl 3 nh 2 Cat.o. 37% as u g g g 10
12 Kanto eagents C K
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寄稿論文 有機合成から現代の錬金術へ | 東京化成工業
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(1) / 130 g 25 g 520% 170 g 30 g 560% 70 mg 600 mg 11.6% 0 10.5 mg 0% (1) (2) / 50100 g 25 g 200400% 50100 g 30 g 167333% 5001000 mg 600 mg 83167% 1020 mg 10.5 mg 95190% (2) / (1) 45.6 g 30 g 152% (2)
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CH 2 H H H CH 2 n-1 H CH 2 n H Potato α-glucan phosphorylase H n soluble starch P i n-1 H P() 2 glucose-1-phosphate Pi H CBPase H glucose P i glucose-1-phospate cellobiose H cellooligosaccharide n+1 CDPase
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TCIメール No.123 | 東京化成工業
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寄稿論文 高い発ガン活性を示す鉄キレートお構造特性 | 東京化成工業
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Mercuric Triflate Revisited: Development of Catalytic Reactions Mugio Nishizawa* and Hiroshi Imagawa Hg(OTf)2, developed in our group in 1983 as an olefin cyclization agent, has been developed further
物理化学I-第12回(13).ppt
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