Evaluation of (+)-sparteine-like diamines for asymmetric synthesis

被引：76

作者：

Dearden, MJ ^{[1
]}

McGrath, MJ ^{[1
]}

O'Brien, P ^{[1
]}

机构：

[1] Univ York, Dept Chem, York YO10 5DD, N Yorkshire, England

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 69卷 / 17期

基金：

英国工程与自然科学研究理事会;

关键词：

D O I：

10.1021/jo049182w

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Three new (+)-sparteine-like diamines were prepared from (-)-cytisine and evaluated as sparteine surrogates in the alpha-lithiation rearrangement of cyclooctene oxide and the palladium(II)/diamine catalyzed oxidative kinetic resolution of I-indanol. The new diamines exhibited opposite enantioselectivity to that observed with (-)-sparteine but increasing the steric hindrance of the N-alkyl group beyond N-Et had a detrimental effect on enantioselectivity. The optimal N-Me diamine was evaluated with much success in five other (-)-sparteine-mediated processes involving different metals (lithium, magnesium, and copper) and different types of reaction mechanisms.

引用

页码：5789 / 5792

页数：4

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