N-propargylamides via the asymmetric Michael addition of B-alkynyl-10-TMS-9-borabicyclo[3.3.2]decanes to N-acylimines

被引：34

作者：

Gonzalez, Ana Z. ^{[1
]}

Canales, Eda ^{[1
]}

Soderquist, John A. ^{[1
]}

机构：

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

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 15期

关键词：

D O I：

10.1021/ol0611595

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The asymmetric synthesis of N-propargylamides through Michael addition of the alkynylborane 1 to N-acylimines is reported. The N-acetylimines provide the best substrates for the process exhibiting high selectivity (56-95% ee) with predictable stereochemistry. In several cases, 5 crystallizes in essentially pure form (97-99% ee) and a single-crystal X-ray structure was also obtained for 5g (R-1 = R-2 = Me, R-3 = o-Cl-C6C4). The process regenerates 4 for its direct conversion back to 1 and facilitates the efficient recovery of the pseudoephedrine.

引用

页码：3331 / 3334

页数：4

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