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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- くうしょう だいほうじ
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1 substrate control reagent control
2 Tf Tf amine H n-u Tf Et 3 3
3 n-u Tf Et syn Tf anti n Tf, Amine (1.3eq) (1.5eq) CH Cl, -78 C n n Z E CH -78 C, 1h; 0 C, 1h n H Triflate Et Tf n-u Tf c-pen Tf Tf Amine Yield (syn:anti) Yield (syn:anti) Yield (syn:anti) Yield (syn:anti) Et 96 (9:8) 97 (95:5) 97 (95:5) 84 (90:10) 93 (95:5) 95 (95:5) 96 (9:8) n-u 3 0 <10 Et 3 0 <10 94 (:78) 9 (10:90) - -C E() Z() E Z amine Tf H With small boron reagent Z()-enolate amine H With bulky boron reagent E()-enolate 4
4 synanti 8-phenylmenthol 8-phenylmenthol anti entry 1 syn syn anti entry 3 syn anti entry 5 entry 1) Tf, Et 3 CH Cl ) CH -78 C, 1h; 0 C, 1h H Entry Tf Et 3 Enolization condition (equiv) (equiv) (T ( C), time) syn:anti Yield (%) , 3h : , 3h : , 1h 84 : , 30min 80 : ,3h; 0, 1h 80 : 0 9 ds for syn 98 : ; for anti 5 : 48 5
5 Tf Et 3 CH H H ss Cl, Et 3 nr, K C 3, CH 3 C 100% reflux, 7 h, 95% H H (-)-orephedrine S s H EtCCl, Py, CH Cl 100% n S s n S s mp 14, 147 C [α] D 11.1 n S s mp 14, 147 C [α] D -11. (+)-1 from (-)-orephedrine (-)-1 from (+)-orephedrine entry 1 n-u Tf Et 3 entry n-u Tf Et syn anti syn syn entry 4 Tf Et anti syn anti anti entry 3 Tf Et 3 anti syn anti entry 5 syn anti n S s 1) Tf, amine ) CH n H H S s n S s [anti] [syn] Entry Tf (eq) Amine (.4eq) Conditions Yield (%) anti : syn 1 n-u Tf Et 3-78 C, h < 3 Ð Et -78 C, h : 87 3 Tf Et 3-78 C, h 95 >99 : 1 4 Et -78 C, h 70 >99 : 1 5 Et 3-78 C h ; 0 C 14 h : 86 ds for anti >30 : 1; for syn >30 : 1 6
6 H n S s Tf (eq), Et 3 (.4eq) CH Cl, -78 C, h CH (1. eq) -78 C 1h; 0 C 1h n S s anti :syn = >98 : Entry CH Yield (%) ds for anti : 3 Et : 4 3 n-pr : : : 5 6 t-u- 96 > 99 : : 5 8 (E)-CH 3 CH=CH : 9 CH =C(CH 3 ) : 4 10 nch CH : 5 11 nch C(CH 3 ) : 4 LiAlH 4, THF, 0 C H H + n H S s H TES n S s 1) TESTf, Lut. -78 C ) DIAH, CH Cl H + H 1) LiH (10eq), THF-H ) CH, ether + 7
7 matched pair mismatched pair n H H (+)-1 (-)-1 H S s = Sit-u n S s >98 : (matched) >10 : 1 (mismatched) syn anti n-u Tf Et syn anti syn syn syn-anti syn anti syn H H (-)-ephedrine 1) HAS Cl, Et 3 ) EtCCl, Py. overall yield >95% HAS 3 HA= 1) n-u Tf, Et ) CH HAS H n syn : anti = >94 : 6 Entry CH Yield (%) ds for syn 1 Et : 3 n-pr- 93 >97 : : 3 4 t-u : : 5 6 (E)-CH 3 CH=CH- 98 >97 : 3 8
8 Tf Et 3 s S n 4 Tf (.5eq), Et 3 (3eq) CH Cl, -78 C, 0.5 h H CH (.5 eq) -78 C 15min; rt 1h H + s S n s S n H 5 (5~0%) 6 (80~95%) s S n 6a H H s S n 6b H H s S n 6c H H H H H s S n s S n s S n 7a [H: δ.6, J = 4.6 and 7.4 Hz] 7b [H: δ.65, J=4.6 and 7.5 Hz] 7c [H: δ.56, t, J=.7 Hz] 9
9 s S n 4 1) Tf (.5eq), Et 3 (3eq) CH Cl, -78 C, 0.5 h ) CH (.5 eq), -78 C, 5min s S H n 5 (88 : 1) H H 8 () 4-methyl-1,3-pentanediol [α] D (c.0, CHCl 3 ) entry 5 atio of bis-aldol Entry CH (chiral a) : (chiral b) : (meso-c) 1-88 : 9 : 3 Et- 90 : 4 : : 3 : : 3 : : Ð : 4* 6 CH =C(CH 3 )- 90 : 4 : 6 *CH Tf complex was added H ss () C PTS, acetone n H ss n 6 7 LiAlH 4 H PDC HC MgX H TFA/H H H H C 3 10
10 Tf (.5eq), Et 3 (3eq) CH Cl, -78 C, 0.5 h s S n 4 H 3 s S n H H C 1) CH (1.0 eq), -78~-0 C 15min ) CH (1.5 eq), -0 C~ rt 1h H H A H 3 s S n 63% H A δ 3.5; H δ.9; H C δ 4.96 J(H A -H )= 5.0 Hz J(H -H C )= 8.0 Hz Tf Et 3 dl meso n 1) Tf (.5 eq), Et 3 (3 eq) CH Cl, -78 C, 0.5 h ) CH (3 eq), -78 C ~ rt y. >95% (dl : meso = >95 : 5) n H H H = n-c 6 H 13 ; y. >98% H S y. >98% S 11
11 ss CH 3 n 4 1) Tf (.0 eq), Et 3 (.4 eq) CH Cl, -78 C, 0.5 h ) SCCH 3 (1 eq) 3) CH * H 73% (mono : bis = 86 : 14) H S not detected 1) Tf (.0 eq), Et 3 (.4 eq) H H CH Cl, -78 C, 0.5 h ) SCCH S 3 (1 eq) 3) CH 98% 50% CH 3 D CH 3 CD ss CH 3 n 4 1) Tf, Et 3 CH Cl, -78 C, 0.5 h ) D, AcD ss n CH D Tf D contents 1.0 eq 1.5 eq.0 eq 47% 73% 9% 1
12 ss n 4 H TIPS n 9 (3 : 1) 4 : 9 = 1 : 1 H ss n 5 5% H 1) Tf (.5 eq), Et 3 (3 eq) CH Cl, -78 C, 0.5 h ss n 6 H 95% (3 : 9 : 88) ) CH (3 eq), -78 C ~ rt Double Aldol eaction H * 10a: with TIPS TIPS n 10b: with ss 9 ecovered Unchanged! X X [ P()(Et )] 13
13 F 3 C CH 3 S ketone; thioester S CF 3 [F] CH 3 F 3 C S S F 3 C [A] CH 3 F 3 C S + Tf - CH 3 H 3 C [] Tf F 3 C S Et 3 CH 3 [G] CH CH C CH [C] Et 3 H:Tf Et 3 H:Tf CH [H] F 3 C S [I] Tf/Et 3 [D] amine [E] 14
14 1) Cowden, C. J.; Paterson, I. rganic eactions, 1997, 51, ) (a) Mukaiyama, T.; Inoue, T. Chem. Lett. 1976, (b) Inoue, T.; Mukaiyama, T. ull. Chem. Soc. Jpn. 1980, 53, ) (a) Masamune, S.; Choy, W.; Kerdersky, F. A. J.; Imperiali,. J. Am. Chem. Soc. 1981, 103, (b) Evans, D. A.; artroli, J.; Shih, T. L. J. Am. Chem. Soc. 1981, 103, 17. 4) (a) Masamune, S.; Choy, W.; Petersen, J. S.; Sita, L.. Angew. Chem. Int. Ed. Engl. 1985, 4, (b) 1986, 44, 309, ) (a) Evans, D. A.; elson, J. V.; Taber, T.. J. Am. Chem. Soc. 1981, 103, (b) rown, H. C.; Dhar,. K.; Ganesan, K.; Singaram,. J. rg. Chem. 199, 57, (c) Ganesan, K.; rown, H. C. J. rg. Chem. 1994, 59, ) I / Et 3 (a) Ganesan, K.; rown, H. C. J. rg. Chem. 1994, 59, 336. (b) Ganesan, K.; rown, H. C. J. rg. Chem. 1994, 59, ) Abiko, A.; Liu, J-F.; Masamune, S. J. rg. Chem. 1996, 61, ) Kim,.-M.; Williams, S. F.; Masamune, S. In Comprehensive rganic Synthesis, Trost,. M., Fleming, I., Eds.; Pergamon Press: xford, 1991; Vol. (Heathcock, C. H., Ed.), Chapter 1.7, p ) Abiko, A.; Liu, J.-F.; Masamune, S. J. Am. Chem. Soc. 1997, 119, ) Abiko, A. rganic Syntheses, in press. 11) Abiko, A., unpublished results. 1) Liu, J.-F.; Abiko, A.; Pei, Z.; uske, D. C.; Masamune, S. Tetrahedron Lett. 1998, 39, ) Abiko, A.; Liu, J.-F.; uske, D. C.; Moriyama, S.; Masamune, S. J. Am. Chem. Soc. 1999, 11, ) (a) LŸtjens, H.; Knochel, P. Tetrahedron: Asymmetry 1994, 5, (b) LŸtjens, H.; Wahl, G.; Moller, F.; Knochel, P. rganometall. 1997, 16, ) Kšster,., Synoradzki, L., Chem. er., 1984, 117, D. Hamilton Award A.C. Cope Scholar Award π Si, Ge,Sn P1371 (1,S)--(-enzyl--mesitylenesulfonyl)amino-1-phenyl-1-propyl Propionate 1g 16,400 P137 (1S,)--(-enzyl--mesitylenesulfonyl)amino-1-phenyl-1-propyl Propionate 1g 16, (1,S)--(-enzyl--mesitylenesulfonyl)amino-1-phenyl-1-propanol 1g 10, (1S,)--(-enzyl--mesitylenesulfonyl)amino-1-phenyl-1- propanol 1g 10,000 A1535 (1S,)--[-enzyl--(mesitylenesulfonyl)amino]-1-phenylpropyl Acetate 1g 14,300 A1534 (1,S)--[-enzyl--(mesitylenesulfonyl)amino]-1-phenylpropyl Acetate 1g 14,300 15
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1 a C CF b c 4 5 Me Me S Jacobsen's catalyst Scheme 1. eagents and conditions: (a) C (1.5 equiv), Jacobsen's catalyst (0.05 equiv), toluene, 0 C, 40 h, then trifluoroacetic anhydride (4.0 equiv), 60 C,
水素移動型不斉還元触媒｜関東化学株式会社
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 67-100% yield, 92-98% ee (S/C = 100-1000) 100% yield dl:meso
CTETS 7 8 9 11 Addition Rf Rf u Rf Rf u u : R, R 2, RS, X etc. Hydrolysisesterification Ewg Ewg H C 3 H C 2 R Ewg Ewg Ewg=C 3, C 2 R' etc. R=H or Alkyl Ewg Ewg RH Base Ewg Ewg R RH Base Ewg Ewg R R Amidation
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22.1 S 2 2 peroxide 72% M.S. Kharasch,.C. own, J. Am. Chem. Soc., 61, 2142 (1939). C 3 C 2 C 2 C 3 2 C 3 C 2 CC 3 h C 3 C 2 C 2 C 2 70% 30% C 3 C 2 C 2 C 3 2 C 3 C 2 CC h 3 C 3 C 2 C 2 C 2 98% 2%. Sing,
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Table 1. A List of Known itrating Agents itric acid Alone or in combination with H 2 S 4, H 3 P 4, H 4, HF(BF 3 ), CF 3 C 2 H, S 3 H, CF 3 S 3 H, FS 3 H(SbF 5 ), sulfonated resins, clays, molecular sieves,
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A Practical Guide to the IUPAC Nomenclature of Organic Compounds Kazuo HATA * The IUPAC nomenclature is not always properly accepted. Many incorrect names are found in contributed papers by many authors.
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