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Org Lett. 2014 Apr 4;16(7):1880-3. doi: 10.1021/ol500302r. Epub 2014 Mar 25.

Regioselective nucleophilic addition of organometallic reagents to 3-geminal bis(silyl) N-acyl pyridinium.

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  • 1Key Laboratory of Drug-Targeting of Education Ministry and Department of Medicinal Chemistry, West China School of Pharmacy, ‡State Key Laboratory of Biotherapy, West China Hospital, §Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University , Chengdu 610041, P. R. China.

Abstract

A regioselective nucleophilic addition to 3-geminal bis(silyl) N-acyl pyridinium has been described. Geminal bis(silane) shows contrasting roles that lead to different regioselectivities for the addition of different nucleophiles: its steric effect dominates to favor 1,6-addition of alkyl, vinyl, and aryl organometallic reagents; its directing effect dominates to favor 1,2-addition of less sterically demanding alkynyl Grignard reagents.

PMID:
24666415
[PubMed - indexed for MEDLINE]
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