Oxyanion orientation in anionic oxy-Cope rearrangements

…, YR Lee, B Moon, O Kwon, MS Shim…

Index: Lee, Eun; Lee, Yong Rok; Moon, Bongjin; Kwon, Ohyun; Shim, Mi Seong; Yun, Jae Sook Journal of Organic Chemistry, 1994 , vol. 59, # 6 p. 1444 - 1456

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Citation Number: 43

Abstract

Efficiency of chirality transfer in anionic oxy-Cope rearrangement depends solely on the orientational preference of the oxyanionic bond in the substrates with a single carbinol carbon chiral center. In chairlike transition-state conformations for the rearrangement of simplest substrates like anions generated from (E)-l-pheny1-1, 5-hexadien-3-01 and (E)-1, 5- heptadien-4-01, the oxyanionic bond is more prone to adopt the pseudoaxial orientation. ...