Stereospecific Synthesis of 1,2,3-Trisubstituted Cyclopropanes from Pseudoglycals
Drisya Chittadi Sankar1, Ramu Sridhar Perali1
1School of Chemistry, University of Hyderabad, C. R. Rao Road, Gachibowli, Hyderabad-500046, India.
Abstract:
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.
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