Structures of reaction intermediates and transition states for the stereoselective asymmetric synthesis of 2-cyclohexen-1-ol using chiral lithium amides : Theoretical prediction of stereoselectivity by MM3 force field

DOI

Bibliographic Information

Other Title
  • キラルリチウムアミド反応剤を用いた２-シクロヘキセン-１-オールの立体選択的不斉合成反応の反応中間体および遷移状態の構造：ＭＭ３分子力場による立体選択性の理論的予測

Description

Chiral 2-cyclohexen-1-ol can be prepared with high enantioselectivity from cyclohexene oxide by using chiral lithium amide reagent. In order to predict the stereoselectivity of this asymmetric reaction theoretically, structures and conformational energies of the reaction intermediate complex composed of cyclohexene oxide and chiral lithium amide were estimated by the MM3 force field. MM3 calculations showed that the reported enantiomer excess (%ee) values determined by experiments could be evaluated well from the populations of the reaction intermediate complexes leading to the (S)- or (R)-enantiomer. Comparisons of the structures of reaction intermediates by the MM3 force field and those of transition state by ab initio calculations were also performed.

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Details 詳細情報について

  • CRID
    1390282680532055296
  • NII Article ID
    130004645150
  • DOI
    10.11494/kisoyuki.18.0.52.0
  • Text Lang
    ja
  • Data Source
    • JaLC
    • CiNii Articles
  • Abstract License Flag
    Disallowed

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