Effects of solvent and lithiating agent on stereoselectivity in lithiation of chiral 1,1'-bis(oxazolinyl)ferrocenes

被引：35

作者：

Park, J ^{[1
]}

Lee, S ^{[1
]}

Ahn, KH ^{[1
]}

Cho, CW ^{[1
]}

机构：

[1] POHANG UNIV SCI & TECHNOL,CTR BIOFUNCT MOL,POHANG 790784,SOUTH KOREA

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 34期

关键词：

D O I：

10.1016/0040-4039(96)01331-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The analysis of phosphorylation products was carried out to investigate the stereoselectivity change in lithiation of 1,1'-bis[(S)-2-(4-R-oxazolinyl)]ferrocene (1) with varying reaction conditions such as solvents, lithiating agents, and temperatures. Monolithiation with butyllithiums in Et(2)O led to the configuration corresponding to (R)-2, while use of THF favors (S)-2. Dilithiation with sec-BuLi or t-BuLi in Et(2)O led to the configuration corresponding to (R,S)-3. However, the step-by step lithiation at different temperatures with sec-BuLi in Et(2)O provided the dilithiated species corresponding to (R,R)-3. sec-BuLi in THF was special to give (S,S)-3 as the major product. Copyright (C) 1996 Elsevier Science Ltd

引用

页码：6137 / 6140

页数：4

共 9 条

[1]

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