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Updated: Apr 5, 2026

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
Asymmetric vinylogous Michael reaction of cyclic enones with silyloxy furans
Amol P Jadhav1, V U Bhaskara Rao, Pradeep Singh
1Department of Chemistry, Indian Institute of Technology, Delhi, Hauz Khas, New Delhi 110-016, India. ravips@chemistry.iitd.ac.in.
Abstract:
The asymmetric vinylogous Michael reaction of cyclohexenone/medium and large cyclic enones with 2-silyloxyfuran is still a synthetic challenge. In this report, we have explored 1,4-conjugate addition of an enantioselective chiral, primary diamine catalyzed, 2-silyloxy furan to various cyclic enones and β-substituted cyclic enones. The reaction provided syn-Michael adducts (cycloalkane connected γ-butenolide) with good yields, diastereo and enantioselectivities. Furthermore, the synthetic potential of these syn-Michael adducts is demonstrated by 1,4-addition of nucleophiles on the butenolide substructure.
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