ChemInform Abstract: Metallated 2-Alkenyl Sulfoximines in Asymmetric Synthesis: Regio- and Stereoselective Synthesis of Highly Substituted Tetrahydrofurans.
Abstract
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ChemInform Abstract
Starting from enantiopure sulfoximines (I), (V), (VII), and the epimer of (V), a one-pot procedure is developed for the synthesis of tri- and tetrasubstituted tetrahydrofurans. Intermediate Tbs-protected alcohols like (III), formed from the above sulfoximes and aldehydes (II), undergo fluoride-ion induced regioselective ring closure. The absolute configuration in the target furans is controlled at C-3 and C-4 by the sulfoxime moiety during aldehyde uptake, at C-2 by the proper choice of aldehyde (II), and at position 5 by the release of 1,3-allylic strain.
