NHC-Catalyzed Formal [2+2] Annulations of Allenoates for the Synthesis of Substituted Oxetanes

Susana S. Lopez, Ashley A. Jaworski, Karl A. Scheidt*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

5 Scopus citations

Abstract

An N-heterocyclic carbene (NHC)-catalyzed reaction of γ-substituted allenoates for the synthesis of substituted oxetanes has been developed. The method provides an approach to access substituted oxetanes in a single step and is the first example of an NHC-catalyzed formal [2+2]-annulation employing γ-substituted allenoates with trifluoromethyl ketones. Mechanistic and modeling studies provide a rationale for the divergence in reactivity observed compared to the analogous reaction using unsubstituted allenoates and inform a hypothesis to explain the observed diastereoselectivity under different reaction conditions.

Original languageEnglish (US)
Pages (from-to)14637-14645
Number of pages9
JournalJournal of Organic Chemistry
Volume83
Issue number23
DOIs
StatePublished - Dec 7 2018

ASJC Scopus subject areas

  • Organic Chemistry

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