Journal of Organic Chemistry p. 5742 - 5745 (1987)
Update date:2022-08-16
Topics:
Denmark, Scott E.
Marlin, John E.
The anions derived 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.
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