1,4-addition reaction of 5H-oxazol-4-ones to vinyl ketones catalyzed by chiral guanidines

被引：13
作者：
Morita, Akane [1 ]
Misaki, Tomonori [1 ]
Sugimura, Takashi [1 ]
机构：
[1] Univ Hyogo, Grad Sch Mat Sci, Kamigori, Hyogo 6781297, Japan
来源：
TETRAHEDRON LETTERS | 2015年 / 56卷 / 01期
关键词：
Organocatalysis; 1,4-addition; 5H-Oxazol-4-one; Chiral guanidine; Quaternary carbon center; HYDROXYCARBOXYLIC ACID-DERIVATIVES; ASYMMETRIC MANNICH REACTIONS; ENANTIOSELECTIVE SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; MICHAEL ADDITION; CONSTRUCTION; ALKYLATION;
D O I：
10.1016/j.tetlet.2014.11.079
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
In this Letter, a chiral guanidine-catalyzed 1,4-addition reaction of 5H-oxazol-4-ones to vinyl ketones is described. The 1,4-addition reaction proceeded with a high enantioselectivity using 5H-oxazol-4-ones, substituted with a 3-chloro-5-methylphenyl group, as pronucleophiles and a newly developed chiral guanidine as a catalyst. The optimized reaction conditions were also effective in achieving excellent enantioselectivity in the 1,6-addition to dienones. Subsequent solvolysis of the 1,4-addition adduct yielded the corresponding alpha-hydroxy-5-oxocarboxylates. (C) 2014 Elsevier Ltd. All rights reserved.
引用
收藏
页码：264 / 267
页数：4
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