Enantio- and Chemoselective Intramolecular Iridium-Catalyzed O-Allylation of Oximes

被引：18

作者：

Sandmeier, Tobias ^{[1
]}

Carreira, Erick M. ^{[1
]}

机构：

[1] ETH ETH Zurich, CH-8093 Zurich, Switzerland

来源：

ORGANIC LETTERS | 2021年 / 23卷 / 07期

基金：

瑞士国家科学基金会;

关键词：

CYCLOADDITION;

D O I：

10.1021/acs.orglett.1c00559

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A method for the enantio- and chemoselective iridium-catalyzed O-allylation of oximes is described. Kinetic resolution in an intramolecular setting provides enantioenriched oxime ethers and aliphatic allylic alcohols. The synthetic potential of the products generated with this method is showcased by their elaboration into a series of heterocyclic compounds and the formal synthesis of glycoprotein GP IIb-IIIa receptor antagonist (-)-roxifiban. Preliminary mechanistic experiments and computational data shed light on the remarkable chemoselectivity of the reaction.

引用

页码：2643 / 2647

页数：5

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