Synthesis of chiral polyfunctionalised cyclopentanes from the Diels-Alder adduct of furan and maleic anhydride

Authors
Brown, RT Jameson, SB Ouali, D Tattersall, PI
Citation
Rt. Brown et al., Synthesis of chiral polyfunctionalised cyclopentanes from the Diels-Alder adduct of furan and maleic anhydride, J CHEM R-S, (4), 2000, pp. 176-178
Citations number
4
Categorie Soggetti
Chemistry
Journal title
JOURNAL OF CHEMICAL RESEARCH-S
ISSN journal
03082342 → ACNP
Issue
4
Year of publication
2000
Pages
176 - 178
Database
ISI
SICI code
0308-2342(200004):4<176:SOCPCF>2.0.ZU;2-F
Abstract
Chiral polyfunctionalised cyclopentanes have been readily obtained in simil ar to 65% enantiomeric excess via a stereospecific Wagner-Meerwein rearrang ement induced by bromination of derivatives of the exo-cis Diels-Alder addu ct of furan and maleic anhydride, combined with desymmetrisation of a meso intermediate by pig liver esterase.