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
收藏
页码：4054 / 4057
页数：4
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