Helvetica chimica acta

Enantioselective Formation of Bicyclic Lactones by Rhodium??Catalyzed Intramolecular CH??insertion reactions

P Müller, P Polleux

Index: Mueller, Paul; Polleux, Philippe Helvetica Chimica Acta, 1994 , vol. 77, p. 645 - 654

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Citation Number: 48

Abstract

Abstract The decomposition of cyclohexyl diazoacetate (5a) in the presence of the chiral [Rh 2 {(2S)-mepy} 4] catalyst leads to a 3: 1 cis/trans mixture of bicyclic lactone 6a with an enantiomeric excess of 95–97%(cis) and 90%(trans). The conformationally rigid tert-butyl derivatives 5b and 5c afford, in the presence of the same catalyst, 6b and 6c, respectively, via insertion into the equatorial C [BOND] H bonds exclusively, with ee's of ca. 95%. A ...