Additions of Organomagnesium Halides to α-Alkoxy Ketones: Revision of the Chelation-Control Model

Jacquelyne A. Read, Yingying Yang, K. A. Woerpel

Research output: Contribution to journalArticle

Abstract

The chelation-control model explains the high diastereoselectivity obtained in additions of organometallic nucleophiles to α-alkoxy ketones but fails for reactions of allylmagnesium halides. Low diastereoselectivity in ethereal solvents results from no chelation-induced rate acceleration. Additions of allylmagnesium bromide to carbonyl compounds are diastereoselective using CH2Cl2 as the solvent even though rate acceleration is still absent. Stereoselectivity likely arises from the predominance of the chelated form in solution. Therefore, a revised chelation-control model is proposed.

Original languageEnglish (US)
Pages (from-to)3346-3349
Number of pages4
JournalOrganic Letters
Volume19
Issue number13
DOIs
StatePublished - Jul 7 2017

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Additions of Organomagnesium Halides to α-Alkoxy Ketones: Revision of the Chelation-Control Model'. Together they form a unique fingerprint.

  • Cite this