Deracemization of diarylmethanes via lateral lithiation-protonation sequences by means of sparteine

被引：33

作者：

Prat, L ^{[1
]}

Mojovic, L ^{[1
]}

Levacher, V ^{[1
]}

Dupas, G ^{[1
]}

Queguiner, G ^{[1
]}

Bourguignon, J ^{[1
]}

机构：

[1] Inst Natl Sci Appliquees Rouen, Lab Chim Organ Fine & Heterocycl IRCOF, Associe CNRS, F-76131 Mont St Aignan, France

来源：

TETRAHEDRON-ASYMMETRY | 1998年 / 9卷 / 14期

关键词：

D O I：

10.1016/S0957-4166(98)00228-6

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Deracemization of diarylmethane derivatives was investigated by lateral lithiation-protonation mediated by (-)sparteine. Treatment of racemic 4-phenyltetrahydroisoquinoline 1 with s-butyllithium-(-)-sparteine followed by protonation of the resulting anion afforded (R)-phenyltetrahydroisoquinoline 1 in up to 88% e.e. Following the same procedure, racemic 2-(1-phenylethyl)pyridine 2 was subjected to the lithiation-protonation sequence. The stereochemical outcome of the sequence proved to be highly dependent on the proton sources giving either (S)- or (R)-2-(1-phenylethyl)pyridine 2 with EtOH or t-BuOH respectively in up to 50% e.e. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：2509 / 2516

页数：8

共 34 条

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