Enantioselective Conia-Ene-Type Cyclizations of Alkynyl Ketones through Cooperative Action of B(C₆F₅)₃, N-Alkylamine and a Zn-Based Catalyst

Min Cao, Ahmet Yesilcimen, Masayuki Wasa*

*Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467, United States, Email: wasabc.edu

M. Cao, A. Yesilcimen, M. Wasa, J. Am. Chem. Soc., 2019, 141, 4199-4203.

DOI: 10.1021/jacs.8b13757

---

see article for more reactions

Abstract

A combination of B(C₆F₅)₃, an N-alkylamine and a BOX-ZnI₂ complex catalyzes an efficient and highly enantioselective Conia-ene-type process. Through cooperative action of B(C₆F₅)₃ and amine, ketones can be converted in situ to the corresponding enolates. A subsequent enantioselective cyclization involving a BOX-ZnI₂-activated alkyne provides various cyclopentenes in very good yield.

see article for more examples

---

---

Key Words

cyclopentenes, Conia-Ene reaction

---

ID: J48-Y2019