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使用二氢萘烷实现铑催化硼酸对烯酮的不对称共轭加成：一种新型手性双膦配体。

Rhodium-Catalyzed Asymmetric Conjugate Additions of Boronic Acids to enones using DIPHONANE: a novel chiral bisphosphine ligand.

作者信息

Vandyck Koen, Matthys Bavo, Willen Mario, Robeyns Koen, Van Meervelt Luc, Van der Eycken Johan

机构信息

Laboratory for Organic and Bioorganic Synthesis, Department of Organic Chemistry, Ghent University, Krijgslaan 281 (S.4), B-9000 Gent, Belgium.

出版信息

Org Lett. 2006 Feb 2;8(3):363-6. doi: 10.1021/ol0522788.

DOI:10.1021/ol0522788
PMID:16435835
Abstract

[reaction: see text] The synthesis of a novel enantiopure C2-symmetric bisphosphine, DIPHONANE, was accomplished starting from 2,5-norbornadione, utilizing (R,R)- and/or (S,S)-(2,3-O-di[(phenylamino)carbonyl]tartaric acid for the resolution of an intermediate phosphineoxide. The application of this ligand in the rhodium-catalyzed asymmetric conjugate addition of boronic acids to cyclic enones provides the 1,4-addition products in good yields (69-98%) and high ee's (78-95% ee). A byproduct arising from a consecutive 1,4-addition and 1,2-addition was also observed.

摘要

[反应：见正文] 一种新型对映体纯的C2对称双膦DIPHONANE的合成，是从2,5-降冰片二酮开始完成的，利用（R，R）-和/或（S，S）-（2,3-O-二[（苯基氨基）羰基]酒石酸来拆分中间体氧化膦。该配体在铑催化的硼酸与环状烯酮的不对称共轭加成中的应用，以良好的产率（69 - 98%）和高对映体过量值（78 - 95% ee）提供了1,4-加成产物。还观察到了由连续的1,4-加成和1,2-加成产生的副产物。

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