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利用原位制备的铑催化剂将芳基硼酸不对称加成到α,β-不饱和羰基化合物的实用方法。

Practical method for asymmetric addition of arylboronic acids to alpha,beta-unsaturated carbonyl compounds utilizing an in situ prepared rhodium catalyst.

作者信息

Lukin Kirill, Zhang Qunying, Leanna M Robert

机构信息

GPRD Process Research and Development, Abbott Laboratories, North Chicago, Illinois 60064, USA.

出版信息

J Org Chem. 2009 Jan 16;74(2):929-31. doi: 10.1021/jo802136j.

Abstract

A new practical method for the asymmetric Michael addition of arylboronic acids to alpha,beta-unsaturated carbonyl compounds utilizing in situ generated chiral rhodium-binap-based catalyst has been developed to address the unavailability of the preformed catalysts. While maintaining high levels of enantioselectivity reported for the preformed catalysts, the new method provides a convenient access to either enantiomeric form of the product and allows for a substantial reductions in both the boronic acid and the catalyst loads.

摘要

为解决预制催化剂难以获得的问题,已开发出一种新的实用方法,该方法利用原位生成的基于手性铑-联萘酚的催化剂,将芳基硼酸不对称迈克尔加成到α,β-不饱和羰基化合物上。在保持预制催化剂所报道的高对映选择性水平的同时,新方法为产物的任意对映体形式提供了便捷的合成途径,并大幅降低了硼酸和催化剂的用量。

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