Spontaneous and diastereoselective aldol reactions of cyclic β-amino ketones in the presence of water

被引：15
作者：
Lazny, Ryszard [1 ]
Nodzewska, Aneta [1 ]
Tomczuk, Iwona [1 ]
机构：
[1] Univ Bialystok, Inst Chem, PL-15399 Bialystok, Poland
来源：
TETRAHEDRON LETTERS | 2011年 / 52卷 / 43期
关键词：
Aldol reaction; Reaction in water; Tropinone; Granatanone; CATALYSIS; DEPROTONATION; PURE;
D O I：
10.1016/j.tetlet.2011.08.107
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Direct aldol reactions of 4-methyl-1-piperidone, tropinone and granatanone (pseudopelletierine) take place spontaneously in the presence of water without any catalyst or additional reagents. The anti/syn-diastereoselectivity of the aqueous aldol reaction depends on the amount of water used. The syn-selectivity of the reaction is probably due to the thermodynamic control. Excellent atom economy and low E factors together with anti-selectivity as high as 98:2 for the tropinone aldol were obtained. (C) 2011 Elsevier Ltd. All rights reserved.
引用
收藏
页码：5680 / 5683
页数：4
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