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.
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页码：3331 / 3334
页数：4
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