C-H Functionalization -Approach for the Synthesis.of 'Chiral* C2-Symmetric 1,5-Cyclooctadiene Ligands

被引：9

作者：

Zhang, Bowen ^{[1
]}

Hollerbach, Michael R. ^{[1
]}

Blakey, Simon B. ^{[1
]}

Davies, Huw M. L. ^{[1
]}

机构：

[1] Emory Univ, Dept Chem, 1515 Dickey Dr, Atlanta, GA 30322 USA

来源：

ORGANIC LETTERS | 2019年 / 21卷 / 24期

关键词：

CATALYZED ASYMMETRIC 1,4-ADDITION; STEREOSELECTIVE FUNCTIONALIZATION; ARYLBORONIC ACIDS; STEERING LIGANDS; DIENE; ALKENES; ALKYL;

D O I：

10.1021/acs.orglett.9b03764

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Chiral cyclooctadiene (COD) derivatives are readily prepared by rhodium-catalyzed 'allylic C H functionalization of COD. Either mono- or difunctionalization of COD is possible generating the products in high yield, diastereoselectivity and enantioselectivity. The double C H functionalization generates C2-symmetric COD derivatives with four new stereogenic centers in >99% ee, which can be readily converted to a series of chiral COD ligands. Preliminary evaluations revealed that the COD ligands can be used in rhod rhod 2-enone, leading to the conjugate addition products in up to 76% ee. um -catalyzed asymmetric arylation of cyclohex-

引用

页码：9864 / 9868

页数：5

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