Phosphine-Catalyzed (3+2)/(3+2) Sequential Annulation of γ-Vinyl Allenoates: Access to Fused Carbocycles

被引：46
作者：
Feng, Jiaxu [1 ,2 ,3 ]
Chen, Yingying [1 ,2 ,3 ]
Qin, Wenhui [1 ,2 ,3 ]
Huang, You [1 ,2 ,3 ]
机构：
[1] Nankai Univ, Coll Chem, State Key Lab, Tianjin 300071, Peoples R China
[2] Nankai Univ, Coll Chem, Inst Elementoorgan Chem, Tianjin 300071, Peoples R China
[3] Collaborat Innovat Ctr Chem Sci & Engn, Tianjin 300071, Peoples R China
来源：
ORGANIC LETTERS | 2020年 / 22卷 / 02期
基金：
中国国家自然科学基金;
关键词：
ASYMMETRIC 3+2 ANNULATIONS; DELTA-ACETOXY ALLENOATES; DIELS-ALDER REACTIONS; 1ST TOTAL-SYNTHESIS; DOMINO REACTION; ENANTIOSELECTIVE SYNTHESIS; SUBSTITUENT ALLENOATES; EFFICIENT METHOD; FACILE ACCESS; CONSTRUCT;
D O I：
10.1021/acs.orglett.9b04176
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The first (3 + 2)/(3 + 2) sequential annulation of gamma-vinyl allenoates with alkylidenemalononitriles enabled by phosphine catalysis has been reported. A broad range of structurally dense tetra- and penta-substituted bicyclic[3,3,0]octene derivatives, containing a quaternary center and three sequential stereogenic center, were synthesized in good to excellent yields. In this approach, three new C-C bonds are formed in one pot, and epsilon C and alpha C of gamma-vinyl allenoate are twoelectrophilic centers, whereas its gamma C exhibits nucleophilic reactivity.
引用
收藏
页码：433 / 437
页数：5
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