通过（S）-尼古丁的还原二硅化反应合成尼古丁衍生物。

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

作者信息

Smith Emilie D, Février Florence C, Comins Daniel L

机构信息

Department of Chemistry, North Carolina State University, Raleigh, 27695-8204, USA.

出版信息

Org Lett. 2006 Jan 19;8(2):179-82. doi: 10.1021/ol052099q.

DOI:10.1021/ol052099q

PMID:16408869

Abstract

[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.

摘要

[反应：见正文] 通过（S）-尼古丁的还原二硅化反应制备了多种新型尼古丁衍生物。用锂粉和三甲基氯硅烷处理尼古丁可高产率得到1,4-双（三甲基硅基）-1,4-二氢尼古丁。加入各种羰基亲电试剂和催化量的四丁基氟化铵可得到C-5取代的尼古丁或1,4-二氢尼古丁衍生物。