Unusual palladium-mediated methylene-addition to the carbonyl of a homochiral polyfunctionalized cyclohexenone, and intramolecular oxirane-ring opening. Efficient synthesis of novel enantiopure 3a,4,5,7a-tetrahydrobenzoxazole derivatives

Rosa M. Ortuño, Javier Ibarzo, Angel Alvarez-Larena, Joan F. Piniella

Research output: Contribution to journalArticleResearchpeer-review

14 Citations (Scopus)

Abstract

Three new enantiopure oxazoline derivatives have been synthesized in good yields from a homochiral 4-benzamido 2-cyclohexenone. The key step involves the unusual palladium-catalyzed methylene-addition to the carbonyl, giving a conjugated epoxide, and subsequent acid-promoted intramolecular oxirane-ring opening via an S N 2′-type process. Copyright © 1996 Elsevier Science Ltd.
Original languageEnglish
Pages (from-to)4059-4062
JournalTetrahedron Letters
Volume37
Issue number23
DOIs
Publication statusPublished - 3 Jun 1996

Fingerprint Dive into the research topics of 'Unusual palladium-mediated methylene-addition to the carbonyl of a homochiral polyfunctionalized cyclohexenone, and intramolecular oxirane-ring opening. Efficient synthesis of novel enantiopure 3a,4,5,7a-tetrahydrobenzoxazole derivatives'. Together they form a unique fingerprint.

Cite this