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

共 50 条

[31] Asymmetric synthesis of all-carbon quaternary spirocycles via a catalytic enantioselective allylic alkylation strategy
Shockley, Samantha E.
Hethcox, J. Caleb
Stoltz, Brian M.
[J]. TETRAHEDRON LETTERS, 2017, 58 (34) : 3341 - 3343
[32] Enantioselective Synthesis of α-Secondary and α-Tertiary Piperazin-2-ones and Piperazines by Catalytic Asymmetric Allylic Alkylation
Korch, Katerina M.
Eidamshaus, Christian
Behenna, Douglas C.
Nam, Sangkil
Horne, David
Stoltz, Brian M.
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (01) : 179 - 183
[33] Asymmetric synthesis of various chiral 5-pyrimidyl-alkanols by the enantioselective alkylation of pyrimidine-5-carbaldehydes with dialkylzincs in the presence of chiral amino alcohols
Shibata, T
Hayase, T
Aiba, Y
Tabira, H
Soai, K
[J]. HETEROCYCLES, 1997, 46 : 235 - 240
[34] METHODS OF ASYMMETRIC SYNTHESIS - ENANTIOSELECTIVE CATALYTIC HYDROGENATION
IZUMI, Y
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1971, 10 (12) : 871 - &
[35] Catalytic Enantioselective Alkylation of Aldehydes with 3-Bromooxindoles
Li, Zhen
Zhang, Xiao-Ming
Zhang, Fu-Min
Tu, Yong-Qiang
[J]. ORGANIC LETTERS, 2023, 25 (39) : 7252 - 7257
[36] Catalytic asymmetric alkylation of aldehydes by using trialkylboranes
Ukon, Takahiro
Harada, Toshiro
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (26) : 4405 - 4407
[37] Catalytic, enantioselective alkylation of α-imino esters using late transition metal phosphine complexes as catalysts
Ferraris, D
Young, B
Dudding, T
Lectka, T
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (18) : 4548 - 4549
[38] DIASTEREOSELECTIVE ALKYLATION OF (DIENE-ALDEHYDE)FE(CO)3 COMPLEXES WITH FUNCTIONALIZED ZINC-COPPER REAGENTS NUCU(CN)ZNL
WANG, JL
HUENG, CH
YEH, MCP
[J]. JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 1994, 41 (02) : 129 - 137
[39] Asymmetric synthesis of 3-quinolylalkylamine by enantioselective alkylation of N-diphenylphosphinyl-3-quinolylimine using chiral β-amino alcohols
Hayase, T
Osanai, S
Shibata, T
Soai, K
[J]. HETEROCYCLES, 1998, 48 (01) : 139 - 144
[40] ENANTIOSELECTIVE ALKYLATION OF CARBONYL-COMPOUNDS - FROM STOICHIOMETRIC TO CATALYTIC ASYMMETRIC INDUCTION
NOYORI, R
SUGA, S
KAWAI, K
OKADA, S
KITAMURA, M
[J]. PURE AND APPLIED CHEMISTRY, 1988, 60 (11) : 1597 - 1606

← 1 2 3 4 5 →