Enantioselective reactions of α-methoxybenzyllithium generated by t-BuLi/chiral bis(oxazoline) complex with aldehydes

被引：32

作者：

Tomooka, K ^{[1
]}

Wang, LF ^{[1
]}

Komine, N ^{[1
]}

Nakai, T ^{[1
]}

机构：

[1] Tokyo Inst Technol, Dept Chem Technol, Meguro Ku, Tokyo 1528552, Japan

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 37期

关键词：

alpha-methoxybenzyllithium; enantioselection; 1,2-diol;

D O I：

10.1016/S0040-4039(99)01365-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The title reaction is shown to afford the corresponding 1,2-diol monomethyl ethers in moderate-to-high levels of % ee (up to 98%) and % de (up to 90% anti), depending markedly on the aldehyde reactivity. The origin of the enantioselectivity is discussed in terms of a dynamic thermodynamic resolution mechanism. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：6813 / 6816

页数：4

共 5 条

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[3] Enantio selective carboxylation of α-methoxybenzyllithium generated via asymmetric lithiation with a t-BuLi/chiral bis(oxazoline) complex
Komine, N
Wang, LF
Tomooka, K
Nakai, T
[J]. TETRAHEDRON LETTERS, 1999, 40 (37) : 6809 - 6812
[4] Enantioselective carbanion cyclization of 5-alkenyl carbamates induced by asymmetric lithiation with s-butyllithium/(-)-sparteine system
Tomooka, K
Komine, N
Sasaki, T
Shimizu, H
Nakai, T
[J]. TETRAHEDRON LETTERS, 1998, 39 (52) : 9715 - 9718
[5] Enantioselective [2,3]-Wittig rearrangement induced by asymmetric lithiation with a t-butyllithium chiral bis(oxazoline) system
Tomooka, K
Komine, N
Nakai, T
[J]. TETRAHEDRON LETTERS, 1998, 39 (31) : 5513 - 5516

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