Base-promoted diastereoselective addition of nitromethane and nitroethane to N-tert-butylsulfinyl imines: synthesis of N-protected α-amino acids and amino ketones

被引：16
|
作者：
Jesus Garcia-Munoz, M.
Dema, Haythem K.
Foubelo, Francisco [1 ]
Yus, Miguel
机构：
[1] Univ Alicante, Fac Ciencias, Dept Quim Organ, E-03080 Alicante, Spain
来源：
TETRAHEDRON-ASYMMETRY | 2014年 / 25卷 / 04期
关键词：
AZA-HENRY REACTIONS; ASYMMETRIC-SYNTHESIS; BUTANESULFINYL IMINES; P-TOLYLSULFINYLIMINES; ALDEHYDES; CONDENSATION; REDUCTION; SYSTEMS; ESTERS;
D O I：
10.1016/j.tetasy.2014.01.010
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
The reaction of N-tert-butylsulfinyl imines with nitromethane or nitroethane in the presence of NaHCO3 under solvent-free reaction conditions gave beta-nitro amine derivatives with reasonable levels of diastereoselectivity. Enantioenriched N-tert-butylsulfinyl protected a-amino acids or a-amino ketones are accessible upon oxidation of the adducts derived from nitromethane or nitroethane, respectively. (C) 2014 Elsevier Ltd. All rights reserved.
引用
收藏
页码：362 / 372
页数：11
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