Enantiopure eta4-(1-sulfinyldiene)iron(0) tricarbonyl complexes as templates for carbocycle construction via ring-closing metathesis
[reaction: see text] Enantiomerically pure 1-(1Z,3E)-sulfinyl iron(0) dienols have been elaborated to bis-olefins capable of undergoing ring-closing metathesis chemistry. Using Grubbs' ruthenium carbene catalyst, a six-membered carbocycle (with one chiral center) and seven-, eight-, and nine-membered carbocycles (with two chiral centers) have been prepared. Novel transformations include the LiClO4-promoted allylation of an alkylidene malonate and a reductive sulfur-carbon bond cleavage to convert a vinyl sulfoxide into an alkene with SmI2.
Paley
RS
Department of Chemistry, Swarthmore College, Pennsylvania 19081, USA. rpaley1@swarthmore.edu
Estroff
LA
Gauguet
JM
Hunt
DK
Newlin
RC