Diastereoselective Additions of Allylmagnesium Reagents to α-Substituted Ketones When Stereochemical Models Cannot Be Used

Nicole D. Bartolo, Krystyna M. Demkiw, Elizabeth M. Valentín, Chunhua T. Hu, Alya A. Arabi, K. A. Woerpel

Research output: Contribution to journalArticlepeer-review

8 Citations (Scopus)

Abstract

The stereoselectivities of reactions of allylmagnesium reagents with chiral ketones cannot be easily explained by stereochemical models. Competition experiments indicate that the complexation step is not reversible, so nucleophiles cannot access the widest range of possible encounter complexes and therefore cannot be analyzed easily using available models. Nevertheless, additions of allylmagnesium reagents to a ketone can still be stereoselective provided that the carbonyl group adopts a conformation that leads to one face being completely blocked from the approach of the allylmagnesium reagent.

Original languageEnglish
Pages (from-to)7203-7217
Number of pages15
JournalJournal of Organic Chemistry
Volume86
Issue number10
DOIs
Publication statusPublished - May 21 2021

ASJC Scopus subject areas

  • Organic Chemistry

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