N???????-Phthalimide as a Site-Protecting and Stereodirecting Group in Rhodium-Catalyzed C-H Functionalization with Donor/Acceptor Carbenes

被引：9

作者：

Chen, Ziyi ^{[1
]}

Cai, Qinyan ^{[1
]}

Boni, Yannick T. ^{[1
]}

Liu, Wenbin ^{[1
]}

Fu, Jiantao ^{[1
]}

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

机构：

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

来源：

ORGANIC LETTERS | 2023年 / 25卷 / 22期

关键词：

STEREOSELECTIVE FUNCTIONALIZATION; ASYMMETRIC-SYNTHESIS; INSERTIONS;

D O I：

10.1021/acs.orglett.3c00844

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The rhodium-catalyzed enantioselective C-H functionalization of unactivated C-H bonds by means of donor/acceptor carbene-induced C-H insertion was extended to substrates containing nitrogen functionality. The rhodium-stabilized donor/acceptor carbenes were generated by rhodium-catalyzed decomposition of aryldiazoacetates. The phthalimido group was the optimum nitrogen protecting group. C-H functionalization at the most sterically accessible methylene site was achieved using Rh-2(S-2-Cl-5-BrTPCP)(4) as catalyst, whereas Rh-2(S-TPPTTL)(4) was the most effective catalyst for C-H functionalization at tertiary C-H bonds and for the desymmetrization of N-phthalimidocyclohexane.

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页码：3995 / 3999

页数：5

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