Preparation of Multisubstituted Enamides via Rhodium-Catalyzed Carbozincation and Hydrozincation of Ynamides

Benoit Gourdet, Mairi E. Rudkin, Ciorsdaidh A. Watts, Hon Wai Lam

Research output: Contribution to journalLiterature reviewpeer-review

Abstract

Rhodium-catalyzed carbozincation of ynamides using diorganozinc reagents or functionalized organozinc halides is described. Using a tri(2-furyl)phosphine-modified rhodium catalyst, the reaction course is altered to hydrozincation when diethylzinc is employed as the organozinc reagent. Trapping of the alkenylzinc intermediates produced in these reactions in further functionalization reactions is possible. Collectively, these processes enable access to a range of multisubstituted enamides in stereo- and regiocontrolled fashion.

Original languageEnglish
Pages (from-to)7849-7858
Number of pages10
JournalJournal of Organic Chemistry
Volume74
Issue number20
DOIs
Publication statusPublished - 16 Oct 2009

Keywords

  • HIGHLY STEREOSELECTIVE-SYNTHESIS
  • RING-CLOSING METATHESIS
  • DIELS-ALDER REACTIONS
  • AZA-CLAISEN REARRANGEMENT
  • C-N
  • ORGANOZINC REAGENTS
  • COUPLING REACTIONS
  • ALKYNYL BROMIDES
  • TERMINAL ALKYNES
  • CHIRAL YNAMIDES

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