Highly Regioselective Construction of Spirocycles via Phosphine-Catalyzed [3 + 2]-Cycloaddition
The Journal of Organic Chemistry2002Vol. 67(25), pp. 8901–8905
Citations Over TimeTop 10% of 2002 papers
Abstract
A direct entry to spirocycles with low to moderate regioselectivity was achieved by triphenylphosphine-catalyzed [3 + 2]-cycloaddition of active exo-methylenecycles (1) and ethyl 2,3-butadienoate (2). The regioselectivity of the reaction was greatly improved by using the bulky tert-butyl ester of the 2,3-butadienoate (5). The regioselectivity of the reaction was further enhanced by using the tert-butyl 2-butynoate as the substrate. This protocol provided an efficient entry to the skeleton of spirocarbocycles, especially spiro[4.n]alkanes.
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