An Intramolecular Titanium-Catalyzed Asymmetric Pauson−Khand Type Reaction1
Journal of the American Chemical Society1999Vol. 121(30), pp. 7026–7033
Citations Over TimeTop 10% of 1999 papers
Abstract
The development of the first catalytic asymmetric Pauson−Khand type cyclization of enynes is described. The active catalyst, (S,S)-(EBTHI)Ti(CO)2 (1), is generated in situ from (S,S)-(EBTHI)TiMe2 (2). A variety of 1,6-enynes can be converted to the corresponding cyclopentenones in high yield (70−94%) with excellent ee's (87−96%). Limitations of the catalyst with respect to substrate structure are discussed. The absolute configurations of several of the enone products have been ascertained, and these assignments represent a reversal with respect to an assignment in the initial report. A rationale for the sense and levels of enantioselectivity for this catalyst is proposed.
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