Deracemization of alkyl diarylmethanes using (-)-sparteine or a chiral proton source

被引：25

作者：

Prat, L ^{[1
]}

Dupas, G ^{[1
]}

Duflos, J ^{[1
]}

Quéguiner, G ^{[1
]}

Bourguignon, J ^{[1
]}

Levacher, V ^{[1
]}

机构：

[1] INSA, IRCOF, CNRS, Lab Chim Organ Fine & Heterocycl, F-76131 Mt St Aignan, France

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 27期

关键词：

deracemization; asymmetric protonation; (-)-sparteine; chiral proton donor;

D O I：

10.1016/S0040-4039(01)00784-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In a first stage, deracemization of 2-(1-phenylethyl)pyridine 1 and chlorpheniramine 2 was investigated in the presence of (-)-sparteine as a chilal ligand. Whereas (R)-2-(1-phenylethyl)pyridine 1 was obtained in 65% ee with 2,6-di-tert-bulyl-4-methylphenol as a proton donor, the opposite stereoselection was observed with EtOH leading to (S)-2-(1-phenylethyl)pyridine 1 in 53% ee, A second methodology making use of (+)-(R)-1-[5-chloro-2-(methylarnino)-phenyl]-1,2,3,4-tetrahydroisoquinoline 4 as a chiral proton source gave higher enantioselectivities, affording (R)-1 and (R)-2 in up to 84 and 75% ee, respectively. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：4515 / 4518

页数：4

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