A cooperative palladium/chiral amine enabled diastereo- and enantioselective [3 + 2] cycloaddition of π-allyl 1,3-dipoles with α,β-unsaturated aldehydes has been developed. A series of highly functionalized cyclopentanes bearing three continuous tertiary stereocenters can be facilely and efficiently obtained in good to excellent yields (51-97%) with synthetically useful diastereo- and enantioselectivity (93-99% ee) under mild reaction conditions. Control experiments and HRMS analyses were conducted to elucidate the possible mechanism. The utility of the current method was demonstrated by the gram-scale synthesis and elaboration of the products into various functionalized cyclopentanes.
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