Phosphine-Catalyzed Asymmetric (3+2) Annulations of δ-Acetoxy Allenoates with β-Carbonyl Amides: Enantioselective Synthesis of Spirocyclic β-Keto γ-Lactams

被引：56

作者：

Ni, Chunjie ^{[1
]}

Chen, Jiangfei ^{[1
]}

Zhang, Yuwen ^{[1
]}

Hou, Yading ^{[1
]}

Wang, Dong ^{[1
]}

Tong, Xiaofeng ^{[1
]}

Zhu, Shou-Fei ^{[2
,3
]}

Zhou, Qi-Lin ^{[2
,3
]}

机构：

[1] Changzhou Univ, Sch Petrochem Engn, Jiangsu Key Lab Adv Catalyt Mat & Technol, 1 Gehu Rd, Changzhou 213164, Peoples R China

[2] Nankai Univ, State Key Lab, Tianjin 300071, Peoples R China

[3] Nankai Univ, Inst Elementoorgan Chem, Tianjin 300071, Peoples R China

来源：

ORGANIC LETTERS | 2017年 / 19卷 / 13期

基金：

中国国家自然科学基金;

关键词：

HIGHLY FUNCTIONALIZED TETRAHYDROPYRIDINES; QUATERNARY STEREOCENTERS; CYCLOADDITION REACTIONS; DOMINO REACTIONS; FACILE ACCESS; ALLENES; ESTERS; ACID; CONSTRUCTION; HETEROCYCLES;

D O I：

10.1021/acs.orglett.7b01717

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

While the phosphine catalysis is a powerful tool for the construction of N-heterocycles, the phosphine-catalyzed annulations toward lactam motif are still extremely scarce. Here, we report the asymmetric (3 + 2) annulations of delta-acetoxy allenoates with beta-carbonyl amides by using the (R)-SITCP catalyst. The delta C and gamma C of allenoate respectively engage in annulation with the alpha C and N of the amide, forging a gamma-lactam with good to excellent stereoselectivity.

引用

页码：3668 / 3671

页数：4

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