Asymmetric synthesis of β-aryl-β-trifluoromethyl-β-aminoarones via Mannich-type reactions of ketone enolates with chiral aryl CF3-substituted N-tert-butanesulfinyl ketimines

被引：24
|
作者：
Liu, Yingle [1 ]
Huang, Yangen [1 ]
Qing, Feng-Ling [1 ,2 ]
机构：
[1] Donghua Univ, Coll Chem Chem Engn & Biotechnol, Shanghai 201620, Peoples R China
[2] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Organofluorine Chem, Shanghai 200032, Peoples R China
来源：
TETRAHEDRON | 2012年 / 68卷 / 25期
基金：
中国国家自然科学基金;
关键词：
Mannich addition; Aminoarone; N-tert-Butanesulfinyl ketimine; Trifluoromethyl; Asymmetric; ALPHA-DIFLUOROMETHYL AMINES; STEREOSELECTIVE-SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; DIASTEREOSELECTIVE ADDITION; ORGANOMETALLIC REAGENTS; ALCOHOLS; OXIDATION;
D O I：
10.1016/j.tet.2012.04.070
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A method for the preparation of chiral beta-aryl-beta-trifluoromethyl-beta-aminoarones has been developed involving the Mannich-type reactions of ketone-derivative enolates with chiral aryl CF3-substituted N-tert-butanesulfinyl ketimines. This method tolerates a wide of aromatic ketones, giving the products in moderate to excellent yields (up to 91%) with good diastereoselectiveties (up to 93:7 dr). Acidic cleavage of the tert-butanesulfinyl group gave optically pure beta-aryl-beta-trifluoromethyl-beta-aminoarones in excellent yields (up to 98%), which can be further transformed into CF3-substituted aziridine derivatives. (C) 2012 Elsevier Ltd. All rights reserved.
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页码：4955 / 4961
页数：7
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