INTRAMOLECULAR ALLYLSTANNANE ALDEHYDE CYCLIZATIONS - STEREOCHEMICAL RESULTS WITH FLEXIBLE TETHERS FOR REACTIONS FORMING VINYLCYCLOHEXANOLS

Authors
KECK GE DOUGHERTY SM SAVIN KA
Citation
Ge. Keck et al., INTRAMOLECULAR ALLYLSTANNANE ALDEHYDE CYCLIZATIONS - STEREOCHEMICAL RESULTS WITH FLEXIBLE TETHERS FOR REACTIONS FORMING VINYLCYCLOHEXANOLS, Journal of the American Chemical Society, 117(23), 1995, pp. 6210-6223
Citations number
33
Categorie Soggetti
Chemistry
Journal title
Journal of the American Chemical Society → ACNP
ISSN journal
00027863
Volume
117
Issue
23
Year of publication
1995
Pages
6210 - 6223
Database
ISI
SICI code
0002-7863(1995)117:23<6210:IAAC-S>2.0.ZU;2-A
Abstract
Intramolecular Lewis acid-promoted cyclization reactions of both (Z)- and (E)-3-phenyl-8-(tri-n-butylstannyl)oct-6-enal and (Z)- and (E)-3-( benzyloxy)-8-(tri-n-butylstannyl)oct-6-enal have been examined using a variety of Lewis acids, specifically BF3 . Et(2)O, CF3CO2H, SnCl4, Ti Cl4, and MgBr2. Thermally promoted cyclizations were also examined. Th e results show that product stereochemistry is a sensitive function of both olefin stereochemistry and Lewis acid. The data acquired in thes e studies also suggest that such reactions are mechanistically more co mplex than previous studies with more constrained systems have reveale d.