Asymmetric synthesis of (diene)Fe(CO)3 complexes by a catalytic enantioselective alkylation using dialkylzincs

被引：28

作者：

Takemoto, Y ^{[1
]}

Baba, Y

Honda, A

Nakao, S

Noguchi, I

Iwata, C

Tanaka, T

Ibuka, T

机构：

[1] Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 6068501, Japan

[2] Osaka Univ, Grad Sch Pharmaceut Sci, Osaka 5650871, Japan

来源：

TETRAHEDRON | 1998年 / 54卷 / 51期

关键词：

aldehydes; alkylation; asymmetric induction; iron and compounds;

D O I：

10.1016/S0040-4020(98)01010-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of meso-(2,4-hexadien-1,6-dial)Fe(CO)(3) complex 1 with several alkylzincs in the presence of 50 mol% of (S)-(+)- diphenyl(diphenyl(1-methylpyrrolidin-2-yl)methanol 6a proceeded with high enantiotopic group- and diastereotopic Face-selectivity to give (2R,6S)-alcohol complexes 2a-c as major products, except in the case with dimethylzinc (>90% de and >98% ee). On the other hand, the methylation of 1 with Me2Zn proceeded with high enantioselectivity by adding 1.8 equiv. of Ti(Oi-Pr)(4) in the presence of 3 mol% of (S,S)-1,2-bis(trifluoromethylsulfonamide)cyclohexane 9a (82% de, 96% ee). The enantioselective alkylation was also applied to the kinetic resolution of racemic (sorbic aldehyde)Fe(CO)(3) complex 10. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：15567 / 15580

页数：14

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