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Abstract
An unexpected tri-n-butylphosphine-catalyzed zipper cyclization of diyne−diones (1a−d) or yne−diones (1e and 1f) is described. Bicyclic ketones (2a, 2b, 2c, 2e, and 2f) with five- or six-membered rings fused to the five-membered ring were obtained from both aliphatic diyne−diones (1a−c) and yne−diones (1e and 1f) having tetra- or pentamethylene spacers. The bicyclic products (2) were produced with high diastereoselectivity.
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