NUCLEOPHILIC-SUBSTITUTION GONE AWRY - A NOVEL CYCLOPROPANATION REACTION WITH A SURPRISING STEREOCHEMICAL OUTCOME

Authors
TORBORG CJ RABASCO JJ KASS SR
Citation
Cj. Torborg et al., NUCLEOPHILIC-SUBSTITUTION GONE AWRY - A NOVEL CYCLOPROPANATION REACTION WITH A SURPRISING STEREOCHEMICAL OUTCOME, Tetrahedron letters, 36(34), 1995, pp. 6025-6028
Citations number
8
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
36
Issue
34
Year of publication
1995
Pages
6025 - 6028
Database
ISI
SICI code
0040-4039(1995)36:34<6025:NGA-AN>2.0.ZU;2-K
Abstract
Lithium triethylborohydride reacts with the triisopropylbenzene sulfon ate ester of 2-methoxy-5,5-dimethyl-2-vinyl-3-cydohexen-1-ol(1) to aff ord 8-methoxy-6,6-dimethylspiro[2.5]oct-4-en (3). Labeling studies rev eal that this novel cyclopropane forming reaction proceeds with retent ion of configuration at the newly formed quaternary center.