Stereoselective Synthesis of Polysubstituted Spiropentanes
Yair Cohen1, Dor Toledano1, Ilan Marek1
1Schulich Faculty of Chemistry, Technion - Israel Institute of Technology, Technion City, Haifa, 32000, Israel.
Abstract:
A new approach to polysubstituted spiropentanes is developed through a regio- and diastereoselective carbometalation of sp2-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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