Synthesis of nicotine derivatives via reductive disilylation of (S)-nicotine.

Autor: Smith ED; Department of Chemistry, North Carolina State University, Raleigh, 27695-8204, USA., Février FC, Comins DL
Jazyk: angličtina
Zdroj: Organic letters [Org Lett] 2006 Jan 19; Vol. 8 (2), pp. 179-82.
DOI: 10.1021/ol052099q
Abstrakt: [reaction: see text] A variety of novel nicotine derivatives were prepared via reductive disilylation of (S)-nicotine. Treatment of nicotine with lithium powder and chlorotrimethylsilane afforded 1,4-bis(trimethylsilyl)-1,4-dihydronicotine in high yield. Addition of various carbonyl electrophiles and a catalytic amount of TBAF provided either C-5 substituted nicotines or 1,4-dihydronicotine derivatives.
Databáze: MEDLINE