Diastereoselective Michael reactions of (1R)-(+)-camphor methyl ketone enolates with nitro olefins

被引:10
|
作者
Palomo, C
Aizpurua, JM
Oiarbide, M
García, JM
González, A
Odriozola, I
Linden, A
机构
[1] Univ Basque Country, Fac Quim, Dept Quim Organ 1, E-20080 San Sebastian, Spain
[2] Univ Publ Navarra, Dept Quim Aplicada, E-31006 Pamplona, Spain
[3] Univ Zurich, Inst Organ Chem, CH-8057 Zurich, Switzerland
关键词
D O I
10.1016/S0040-4039(01)00885-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The reaction of the sodium enolate of the methyl ketone 2 with a range of nitro olefins proceeds readily to give the corresponding Michael adducts in good yields and diastereoselectivities. Subsequent oxidative cleavage of the acyloin moiety provides gamma -nitroalkanoic acids along with (1R)-(+)-camphor, the chiral auxiliary of the process. which can be recovered and reused. (C) 2001 Elsevier Science Ltd. Ali rights reserved.
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页码:4829 / 4831
页数:3
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