One-Pot Synthesis of Optically Enriched 2-Piperidinones from Aliphatic Aldehydes and Cyanoacrylamides

被引：12

作者：

He, Ying ^{[1
]}

Kang, Tai-Ran ^{[1
,2
]}

Liu, Quan-Zhong ^{[1
]}

Chen, Lian-Mei ^{[1
]}

Tu, Yi-Lian ^{[1
]}

Liu, Ya-Jun ^{[1
]}

Chen, Tang-Bin ^{[1
]}

Wang, Zhi-Qiang ^{[1
]}

Liu, Jie ^{[2
]}

Xie, Yong-Mei ^{[2
]}

Yang, Jin-Liang ^{[2
]}

He, Long ^{[1
]}

机构：

[1] China West Normal Univ, Chem Synth & Pollut Control Key Lab Sichuan Prov, Coll Chem & Chem Engn, Nanchong 637009, Peoples R China

[2] Sichuan Univ, West China Hosp, State Key Lab Biotherapy, Chengdu 610041, Peoples R China

来源：

ORGANIC LETTERS | 2013年 / 15卷 / 16期

基金：

中国国家自然科学基金;

关键词：

ORGANOCATALYTIC MICHAEL ADDITION; DIELS-ALDER REACTION; ASYMMETRIC ALPHA-AMINATION; DOUBLE-MANNICH REACTION; ENANTIOSELECTIVE SYNTHESIS; CONJUGATE ADDITIONS; CASCADE CYCLIZATION; EFFICIENT ACCESS; DOMINO REACTIONS; FORMAL SYNTHESIS;

D O I：

10.1021/ol401951g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly stereoselective one-pot reaction of aliphatic aldehydes and cyanoacrylamides has been developed. The one-pot reaction includes an organocatalytic Michael addition followed by an intramolecular hemiaminalization. After reduction, optically enriched 2-piperidinones with three contiguous chiral centers were obtained in up to 95% yield and 9:1 dr with 99% ee.

引用

页码：4054 / 4057

页数：4

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