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Asymmetric oxidation of silyl enol ethers using chiral dioxiranes derived from α-fluoro cyclohexanones

被引：17
作者：
Solladié-Cavallo, A
Lupattelli, P
Jierry, L
Bovicelli, P
Angeli, F
Antonioletti, R
Klein, A
机构：
[1] Univ Strasbourg, CNRS, Lab Stereochim Organomet, ECPM, F-67087 Strasbourg, France
[2] Univ Basilicata, Dipartimento Chim, I-85100 Potenza, Italy
[3] Univ Roma La Sapienza, Dipartimento Chim, Ist Chim Biomol, CNR,Sez Roma co, Rome, Italy
来源：
TETRAHEDRON LETTERS | 2003年 / 44卷 / 34期
关键词：
fluoro cyclohexanone; dioxiranes; asymmetric oxidation; alpha-hydroxyketone;
D O I：
10.1016/S0040-4039(03)01388-1
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Asymmetric oxidation of silyl enolethers derived from tetralone, 2-methyl-tetralone, propiophenone and deoxybenzoin using chiral dioxiranes generated in situ from oxone and new chiral a-fluorinated cyclohexanones or fructose-derived ketone have been studied. It was observed that tetrasubstituted silyl enolethers are poor substrates, that substitution at C8 of the fluoro-ketones has a significant effect on the enantioselectivities obtained and that the fructose-derived-ketone provides higher enantioselectivities. The absolute configuration of the major hydroxy ketones obtained can be rationalized using a spiro model proposed for epoxidation of olefins. (C) 2003 Elsevier Ltd. All rights reserved.
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收藏
页码：6523 / 6526
页数：4
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