Enantioselective Bromolactonization Using an S-Alkyl Thiocarbamate Catalyst

被引：159

作者：

Jiang, Xiaojian ^{[1
]}

Tan, Chong Kiat ^{[1
]}

Zhou, Ling ^{[1
]}

Yeung, Ying-Yeung ^{[1
]}

机构：

[1] Natl Univ Singapore, Dept Chem, Singapore 117543, Singapore

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2012年 / 51卷 / 31期

关键词：

asymmetric catalysis; cyclization; lactones; Lewis bases; natural products; HIGHLY EFFICIENT SYNTHESIS; LEWIS-BASE CATALYSIS; ASYMMETRIC BROMOLACTONIZATION; IODOLACTONIZATION; COMPLEXES; HALOLACTONIZATIONS; BROMOCYCLIZATION; HALOCYCLIZATION; IODOCYCLIZATION; REARRANGEMENT;

D O I：

10.1002/anie.201202079

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The apple never falls far from the tree: S-alkyl thiocarbamate 1 (see scheme, NBP=N-bromophthalimide) was prepared in high yield through a synthetic sequence involving a Newman-Kwart rearrangement of the corresponding O-alkyl thiocarbamates. Compound 1 was used to catalyze bromolactonization, thus providing enantioenriched δ-lactones in excellent yield and enantioselectivity. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：7771 / 7775

页数：5

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