Solvent-induced stereospecific isomerization of an allylic alcohol to a homoallylic alcohol catalyzed by a chiral lithium amide

PI Arvidsson, M Hansson, AZQ Khan…

Index: Arvidsson, Per I.; Hansson, Maria; Khan, Agha Zul-Qarnain; Ahlberg, Per Canadian Journal of Chemistry, 1998 , vol. 76, # 6 p. 795 - 799

Full Text: HTML

Citation Number: 9

Abstract

Deprotonation of cyclohexene oxide, 1, by lithium (S)-2-(1-pyrrolidinylmethyl) pyrrolidide, 2- Li, on changing the solvent from tetrahydrofuran (THF) to, for example, 2, 5- dimethyltetrahydrofuran (DMTHF) or diethyl ether (DEE) has been shown to yield, besides the lithium alkoxide of 2-cyclohexene-1-ol, 3-Li, the lithium alkoxide of the homoallylic alcohol 3-cyclohexene-1-ol, 4-Li. It was shown that compound 4-Li is formed from 3-Li. No ...

Related Articles:

Syntheses with organoboranes. IX. Vinyl-and 1-alkenyldichloroboranes as ethylene and 1-alkene equivalents for the Diels–Alder reaction

[Zaidlewicz, Marek; Binkul, Jacek R.; Sokol, Wojciech Journal of Organometallic Chemistry, 1999 , vol. 580, # 2 p. 354 - 362]

Evaluation of the use of mandelate derivatives to determine the enantiomeric purity and the absolute configuration of secondary cyclohexenols

[Sarotti, Ariel M.; Pisano, Pablo L.; Pellegrinet, Silvina C. Arkivoc, 2011 , vol. 2011, # 7 p. 343 - 357]

More Articles...