MERCURI-DESILYLATION OF CHIRAL CYCLOPROPYLMETHYLSILANES

Authors
LANDAIS Y PARRARAPADO L
Citation
Y. Landais et L. Parrarapado, MERCURI-DESILYLATION OF CHIRAL CYCLOPROPYLMETHYLSILANES, Tetrahedron letters, 37(8), 1996, pp. 1209-1212
Citations number
24
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
37
Issue
8
Year of publication
1996
Pages
1209 - 1212
Database
ISI
SICI code
0040-4039(1996)37:8<1209:MOCC>2.0.ZU;2-R
Abstract
Mercuri-desilylation of cyclopropylmethylsilanes such as 1 has been sh own to occur with high regioselectivity. The cyclopropane ring-opening followed by desilylation proceeds stereospecifically to afford the co rresponding olefins in good yields. The mercuri-mediated opening of cy clopropylmethyl alcohol analogues gives the opposite regioselectivity and affords only the tetrahydrofuran through a 5-endo-trig cyclization .