Enantiopure η4-(1-Sulfinyldiene)Iron(0) Tricarbonyl Complexes as Templates for Carbocycle Construction via Ring-Closing Metathesis

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Abstract

[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.

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