P(RNCH2CH2)3N:: Efficient 1,4-addition catalysts

被引：91

作者：

Kisanga, PB ^{[1
]}

Ilankumaran, P ^{[1
]}

Fetterly, BM ^{[1
]}

Verkade, JG ^{[1
]}

机构：

[1] Iowa State Univ Sci & Technol, Dept Chem, Ames, IA 50011 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2002年 / 67卷 / 11期

关键词：

D O I：

10.1021/jo010228k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The 1,4-addition of primary alcohols, higher nitroalkanes, and a Schiff's base of an alpha-amino ester to alpha,beta-unsaturated substrates produces the corresponding products in moderate to excellent yields when carried out at -63 to 70 degreesC in the presence of catalytic amounts of the nonionic strong bases P(RNCH2CH2)(3)N (R = Me, i-Pr, i-Bu) in isobutyronitrile. Diastereoselectivity for the anti form of the product is high in the case of the Schiff's base in the absence of lithium ion. These catalysts are easily removed from the product by either column filtration through silica gel or via aqueous workup.

引用

页码：3555 / 3560

页数：6

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