Efficient addition reaction of bromonitromethane to aldehydes catalyzed by NaI:: A new route to 1-bromo-1-nitroalkan-2-ols under very mild conditions

被引：24
|
作者：
Concellon, Jose M.
Rodriguez-Solla, Humberto
Concellon, Carmen
Garcia-Granada, Santiago
Rosario Diaz, M.
机构：
[1] Univ Oviedo, Dept Quim Organ & Inorgan, Fac Quim, E-33071 Oviedo, Spain
[2] Univ Oviedo, Dept Quim Fis & Analit, Fac Quim, E-33071 Oviedo, Spain
来源：
ORGANIC LETTERS | 2006年 / 8卷 / 26期
关键词：
D O I：
10.1021/ol062451f
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A catalytic NaI-mediated novel synthesis of 1-bromo-1-nitroalkan-2-ols was carried out by reaction of bromonitromethane with a variety of aldehydes, under very mild conditions. When the reaction was performed with chiral N, N- dibenzyl alaninal, the corresponding enantiopure ( 1 S, 2 S, 3 S)- 3- dibenzylamino- 1- bromo- 1- nitrobutan- 2- ol was obtained with good stereoselectivity. The structure of this enantiopure bromohydrin was established by X- ray analysis.
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页码：5979 / 5982
页数：4
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