Stereospecific Synthesis of 1,2,3-Trisubstituted Cyclopropanesfrom Pseudoglycals

Strategic design for constructing optically pure 1,2,3-trisubstituted cyclopropanes with three contiguous stereocenters represents a formidable challenge in synthetic organic chemistry. Herein, we report a simple and highly enantio­specific transformation of pseudo­glycals into chiral 1,2,3-trisubstituted cyclopropanes, featuring three consecutive stereocenters, involving a stereospecific [1,4]-Wittig rearrangement. The effects of functional group orientation and conformational preferences were studied. Successful gram-scale preparations and subsequent derivatization reactions yielded various cyclopropane scaffolds with multiple stereocenters.