Phosphine-Catalyzed [4+2] Annulation of Allenoate with Sulfamate-Derived Cyclic 'mines: A Reaction Mode Involving γ′-Carbon of α-Substituted Allenoate

被引：56

作者：

Mao, Biming ^{[1
]}

Shi, Wangyu ^{[1
]}

Liao, Jianning ^{[1
]}

Liu, Honglei ^{[1
]}

Zhang, Cheng ^{[1
]}

Guo, Hongchao ^{[1
,2
]}

机构：

[1] China Agr Univ, Dept Appl Chem, Beijing 100193, Peoples R China

[2] Beijing Univ Chem Technol, State Key Lab Chem Resource Engn, Beijing 100029, Peoples R China

来源：

ORGANIC LETTERS | 2017年 / 19卷 / 23期

关键词：

ASYMMETRIC TOTAL-SYNTHESIS; N-ACYL AMINOPHOSPHINES; 3+2 CYCLOADDITION; AZOMETHINE IMINES; ALPHA; BETA-UNSATURATED IMINES; FUNCTIONALIZED CYCLOPENTENES; ENANTIOSELECTIVE SYNTHESIS; CHIRAL PHOSPHINES; FORMAL SYNTHESES; ALLENIC ESTERS;

D O I：

10.1021/acs.orglett.7b03175

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A phosphine-catalyzed [4 + 2] cycloaddition of cyclic alpha-substituted allenoates with sulfamate-derived cyclic imines has been reported. Using dibenzylphenylphosphine as the nucleophilic catalyst, the reaction worked efficiently to yield various fused multicyclic heterocyclic compounds in high yields with excellent diastereoselectivities. It undergoes a new reaction mode involving gamma'-carbon of alpha-substituted allenoate.

引用

页码：6340 / 6343

页数：4

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