Functionalised bicyclic alcohols by enantioselective alpha-deprotonation-rearrangement of meso-epoxides

Authors
Hodgson, DM Cameron, ID Christlieb, M Green, R Lee, GP Robinson, LA
Citation
Dm. Hodgson et al., Functionalised bicyclic alcohols by enantioselective alpha-deprotonation-rearrangement of meso-epoxides, J CHEM S P1, (18), 2001, pp. 2161-2174
Citations number
59
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
ISSN journal
14727781 → ACNP
Issue
18
Year of publication
2001
Pages
2161 - 2174
Database
ISI
SICI code
1472-7781(20010921):18<2161:FBABEA>2.0.ZU;2-K
Abstract
Enantioselective alpha -deprotonation-rearrangement of achiral substituted cyclooctene oxides 7, 27 and 28 and N-Boc hexahydroazonine oxide 45 using o rganolithiums in the presence of (-)-sparteine 3 or (-)-alpha -isosparteine 4 gives the functionalised bicyclo[3.3.0]octan-2-ols 9, 29, and 32 and ind olizinol 47 in 50-72% yields and 83-89% ees.