A remarkable temperature effect in the desymmetrisation of bridged meso-tricyclic succinic anhydrides with chiral oxazolidin-2-ones

被引：6

作者：

Chaubey, Narendra R. ^{[1
]}

Ghosh, Sunil K. ^{[1
]}

机构：

[1] Bhabha Atom Res Ctr, Div Bioorgan, Mumbai 400085, Maharashtra, India

来源：

RSC ADVANCES | 2011年 / 1卷 / 03期

关键词：

CYCLIC ANHYDRIDES; ASYMMETRIC DESYMMETRIZATION; ENANTIOSELECTIVE SYNTHESIS; METHANOLYTIC DESYMMETRIZATION; BIFUNCTIONAL ORGANOCATALYST; ENANTIOMERICALLY PURE; AMINO-ACID; REVERSAL; CATALYST; ESTERIFICATION;

D O I：

10.1039/c1ra00483b

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A temperature dependent reversal of diastereoselectivity was observed in the desymmetrisation of bridged meso-tricyclic succinic anhydrides with lithiated chiral oxazolidin-2-ones that appears to be kinetically driven at low temperature while the reversibility of the reaction sets in at higher temperatures and thermodynamics governs the reaction outcome.

引用

页码：393 / 396

页数：4

共 2 条

[1] An efficient asymmetric desymmetrization of prochiral glutaric anhydrides with SuperQuat chiral oxazolidin-2-ones
Chaubey, Narendra
Date, Sonali M.
Ghosh, Sunil K.
TETRAHEDRON-ASYMMETRY, 2008, 19 (23) : 2721 - 2730
[2] Practical synthesis of diastereoisomers by a temperature-guided reversal of diastereoselectivity in the desymmetrization of meso-bridged anhydrides with a chiral oxazolidin-2-one
Chaubey, Narendra R.
Wadawale, Amey P.
Ghosh, Sunil K.
TETRAHEDRON-ASYMMETRY, 2013, 24 (19) : 1212 - 1217

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