Journal
TETRAHEDRON
Volume 56, Issue 25, Pages 4267-4277Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/S0040-4020(00)00353-7
Keywords
samarium(II) iodide; 8-endo-dig cyclization; cyclooctenols; hexahydronaphthalenes; sonogashira reaction; siloxycyclopropanes
Categories
Ask authors/readers for more resources
Ketoesters 3a-3h with an alkynylaryl substituent were prepared by standard methods starting from siloxycyclopropanes 6a and 6b. Their reactions with 2.2 equiv. of samarium diiodide in the presence of hexamethyl phosphoramide either produced benzannulated cyclooctenol derivatives 4b (or lactone 9), 4f, 4g, and 4h or hexahydronaphthalene derivatives 5a, 5c, and 5d. The competition between 8-endo-dig and 6-trig cyclizations strongly depends on the substitution pattern of 3. Plausible explanations for this competition and of the diastereoselectivity observed are presented in this paper. (C) 2000 Elsevier Science Ltd. All rights reserved.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available