Asymmetric synthesis of isomerically pure allenyl boranes from alkynyl boranes through a 1,2-insertion-1,3-borotropic rearrangement

被引：46

作者：

Canales, Eda ^{[1
]}

Gonzalez, Ana Z. ^{[1
]}

Soderquist, John A. ^{[1
]}

机构：

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

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2007年 / 46卷 / 03期

关键词：

asymmetric synthesis; boranes; borotropic rearrangement; cumulenes; homopropargylic alcohols;

D O I：

10.1002/anie.200603467

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Razzle-dazzle... and allenyl boranes 1 are obtained in enantiomerically pure form from 2 through a novel CHTMS insertion followed by a sterically driven suprafacial 1,3-borotropic rearrangement. Asymmetric allenylboration with 1 gives syn β-trimethylsilyl (TMS) homopropargylic alcohols 3 in 80-96 % yield with d.r. 99:1 and 94-99 % ee. When R = isopropenyl, allylboration occurs to provide the 1,2,3-trienyl alcohol 4 with >99 % ee. (Chemical Equation Presented). © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：397 / 399

页数：3

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