Highly Regioselective Construction of Spirocycles via Phosphine-Catalyzed [3 + 2]-Cycloaddition
journal contributionposted on 12.11.2002, 00:00 by Yishu Du, Xiyan Lu, Yihua Yu
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.