Abstract
AbstractThe 1,3‐dipolar cycloaddition reactions of chiral five‐membered cyclic azomethine ylides, generated in situ from ethyl glyoxylate and protected (3S,4S)‐dihydroxypyrrolidines 3 and 6 have been studied. The facial selectivity of the cycloaddition reaction is governed by the steric effect of the substituent on the pyrrolidine ring next to the azomethine ylide functionality, leading in all cases to an exclusive Si face approach of the dipolarophile. The exo/endo selectivity depends on the dipolarophile and on the size of the other substituent on the pyrrolidine ring. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)
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