Carbanion-Accelerated Claisen Rearrangements. 4. Asymmetric Induction via l,3,2-Oxazaphosphorinanesla

Scott E Denmark, John E. Marlin

Research output: Contribution to journalLetter

Abstract

The anions dervied from allyl vinyl ethers 1 and 2 undergo rapid and highly selective Claisen rearrangements. The degree of asymmetric induction has been found to be uniformly high (ca. 90:10) for various substituent patterns but depends markedly on the presence of lithium cations. The absolute sense of asymmetric induction has been established using chiral, nonracemic 1.3.2- oxazaphosphorinane 2. Two proposals for the transition structures of the phosphorus-stabilized anions are discussed.

Original languageEnglish (US)
Pages (from-to)5742-5745
Number of pages4
JournalJournal of Organic Chemistry
Volume52
Issue number26
DOIs
StatePublished - Dec 1 1987

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ASJC Scopus subject areas

  • Organic Chemistry

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