Nonracemic α-allenyl carbinols from asymmetric propargylation with the 10-trimethylsilyl-9-borabicyclo[3.3.2]decanes

被引：45

作者：

Hernandez, E ^{[1
]}

Soderquist, JA ^{[1
]}

机构：

[1] Univ Puerto Rico, Dept Chem, Rio Piedras, PR 00931 USA

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 24期

关键词：

D O I：

10.1021/ol051886k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The asymmetric propargylboration of aldehydes at -78 degrees C in < 3 h with 1 provides silylated alpha-allenyl carbinols 6 (60-87%) in high ee (94% to > 98% ee). The reagents 1 are easily prepared in both enantiomeric forms with a simple Grignard procedure and air-stable borinate complexes 2. The ozonolysis of 6 proceeds smoothly through an acylsilane intermediate to give a TMS ester, which is hydrolyzed to the a-hydroxy acid quantitatively with water.

引用

页码：5397 / 5400

页数：4

共 21 条

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