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Keywords:

  • Carbocycles;
  • Allylation;
  • Dia­stereoselectivity;
  • Indium;
  • Lactones;
  • Configuration determination

Abstract

A highly stereoselective protocol is reported for customizing functionalized carbocyclic building blocks (β-hydroxy esters) and bicyclic lactones with a stereoarray that contains contiguous tertiary carbinol and all-carbon stereocenters. The efficient asymmetric induction and diastereofacial selective addition of allyl and propargyl indiums to hindered α,α-disubstituted cycloalkanones is presented. The stereochemistry of representative products was unequivocally established from single-crystal X-ray crystal structure analyses, and a plausible reaction pathway was proposed to support the high diastereofacial selectivity.