Stereoselective Synthesis of Polysubstituted Spiropentanes.
Yair CohenDor ToledanoIlan MarekPublished in: Journal of the American Chemical Society (2022)
A new approach to polysubstituted spiropentanes is developed through a regio- and diastereoselective carbometalation of sp 2 -disubstituted cyclopropenes. The control of selectivity originates from a combined syn -facial diastereoselective carbometalation with a regio-directed addition. The regio-controlling element subsequently serves as a leaving group in an intramolecular nucleophilic substitution. This method allows the preparation of various polysubstituted spiropentanes with up to five contiguous stereocenters.
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