Synlett 2006(3): 0364-0368  
DOI: 10.1055/s-2006-926240
LETTER
© Georg Thieme Verlag Stuttgart · New York

The Nicholas-Type Activation of Cyclopropanes toward Reactions with ­Nitrones in the Homo-[3+2]-Dipolar Cycloaddition

Terry P. Lebold, Cheryl A. Carson, Michael A. Kerr*
Department of Chemistry, The University of Western Ontario, London, Ontario, N6A 5B7, Canada
Fax: +1(510)6613022; e-Mail: makerr@uwo.ca;
Further Information

Publication History

Received 22 September 2005
Publication Date:
06 February 2006 (online)

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Abstract

2-Ethynyl-1,1-carboethoxyclopropane, when treated with Co2(CO)8, results in the formation of the Co2(CO)6 adduct which in turn undergoes smooth cycloaddition in the presence of Sc(OTf)3 to form the corresponding tetrahdyro-1,2-oxazines. The adducts can either be decomplexed to yield the parent acetylenes or made to undergo Pauson-Khand reactions to form 6-cyclo­pentenyltetrahydro-1,2-oxazines.