Synthesis of Highly Functionalized Azabicycles via 2-Alkenyl Sulfoximines

Abstract

Functionalized cycloalkanones have been converted into enantiomerically pure endocyclic 2-alkenyl sulfoximines. Titanated derivatives thereof undergo highly diastereoselective γ-hydroxyalkylation reactions with various amino aldehydes yielding isomerically pure vinyl sulfoximines, which can be cyclized by N-deprotection. The resulting heterobicyclic systems are expected to be interesting scaffolds for the synthesis of topological mimetics of peptides.

amino aldehydes - asymmetric synthesis - bicyclic compounds - metallation - sulfoximines

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