Inverse Temperature Dependence in the Diastereoselective Addition of Grignard Reagents to a Tetrahydrofurfural

被引：15

作者：

Mowat, Jeffrey ^{[2
]}

Kang, Baldip ^{[2
]}

Fonovic, Branden ^{[1
]}

Dudding, Travis ^{[1
]}

Britton, Robert ^{[2
]}

机构：

[1] Brock Univ, Dept Chem, St Catharines, ON L2S 3A1, Canada

[2] Simon Fraser Univ, Dept Chem, Burnaby, BC V5S 1S6, Canada

来源：

ORGANIC LETTERS | 2009年 / 11卷 / 10期

基金：

加拿大自然科学与工程研究理事会;

关键词：

PATERNO-BUCHI REACTION; ORGANOMETALLIC REAGENTS; L-FUCOPYRANOSE; STEREOSELECTIVITY; ISOINVERSION; DERIVATIVES; SELECTIVITY; MODEL; (6S,7S,9R,10R)-6,9-EPOXYNONADEC-18-ENE-7,10-DIOL; REGIOSELECTIVITY;

D O I：

10.1021/ol900324s

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A remarkable example of inverse-temperature-dependent diastereoselectivity was uncovered while investigating the addition of Grignard reagents to a 3-hydroxytetrahydrofurfural. The free hydroxyl group in the tetrahydrofurfural was found to play a key role in these processes, a result corroborated through a series of DFT calculations that also highlighted an entropic preference for the formation of one diastereomer.

引用

页码：2057 / 2060

页数：4

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