Abstract
AbstractHighly enantioenriched 4‐hydroxy‐1‐alkenyl N,N‐diisopropylcarbamates, easily available by asymmetric homoaldol reaction, cyclize by treatment with sodium hydride to form (1r,2t,3t)‐configured 1‐acylcyclopropanes with high diastereoselectivity. The decisive steps are the migration of the N,N‐diisopropylcarbamoyl group onto the alkoxide oxygen atom, followed by an intramolecular homoallylic substitution reaction of the intermediate γ‐carbamoyloxy enolate with inversion of the configuration at the γ‐C atom. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)
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