The Journal of Organic Chemistry

Carbanion-accelerated Claisen rearrangements. 4. Asymmetric induction via 1, 3, 2-oxazaphosphorinanes

SE Denmark, JE Marlin

Index: Denmark, Scott E.; Marlin, John E. Journal of Organic Chemistry, 1987 , vol. 52, # 26 p. 5742 - 5745

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Citation Number: 40

Abstract

Summary: 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. 9010) 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 ...