Diastereoselective alkylations of chiral, phosphorus-stabilized carbanions:: N-alkyl substituent effects in P-alkyl-1,3,2-diazaphosphorinane 2-oxides

被引：14

作者：

Denmark, SE ^{[1
]}

Kim, JH ^{[1
]}

机构：

[1] Univ Illinois, Dept Chem, Roger Adams Lab 245, Urbana, IL 61801 USA

来源：

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE | 2000年 / 78卷 / 06期

关键词：

phosphonamide-stabilized carbanions; alkylation; asymmetric; stereoselective; organolitihium;

D O I：

10.1139/cjc-78-6-673

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A systematic study of the diastereoselective alkylation of anions derived from racemic N-substituted P-alkyl 1,3,2-diazaphosphorinane 2-oxides was carried out with variation of the N-substituent. High diastereoselectivity for the methylation of a P-benzyl anion has been achieved with N-neopentyl derivative 5d. Similarly, a P-ethyl anion derived from N-neopentyl derivative 6d showed high diastereoselectivity upon benzylation. The observed difference in alkylation diastereoselectivity between P-ethyl and P-benzyl anions for various N-alkyl substituents is discussed.

引用

页码：673 / 688

页数：16