Journal
ORGANIC LETTERS
Volume 8, Issue 15, Pages 3331-3334Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol0611595
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- NIGMS NIH HHS [S06GM8102] Funding Source: Medline
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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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