Studies of The Reactivity of (1R,1′R)-3-exo, 3′-exo-Bicamphor; Preparation of New 3-exo, 3′-exo-Bibornane Derivatives

Jean-Olivier Durand

doi:10.1055/s-1999-3478

Synthesis 1999; 1999(5): 835-838
DOI: 10.1055/s-1999-3478

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Studies of The Reactivity of (1R,1′R)-3-exo, 3′-exo-Bicamphor; Preparation of New 3-exo, 3′-exo-Bibornane Derivatives

Jean-Olivier Durand^*

^*UMR 5637, case 007, Université Montpellier 2, Place Eugène Bataillon, 34095 Montpellier cedex 05, France; Fax +33(4)67 14 38 52; E-mail: durand@univ-montp2.fr

Abstract

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The preparative conversion of (1R,1′R)-3-exo, 3′-exo-bicamphor (1) in different useful 3-exo, 3′-exo-bibornane derivatives has been explored. The reactivity of bibornane type molecules was controlled by steric factors which made those products recalcitrant towards functionalisation and led to unusual behaviour. Nevertheless the synthesis of the monophosphine alcohol 9 was achieved in 4 steps and in 25% overall yield after a methylenation hydroboration-oxidation methodology applied to (1R,1′R)-3-exo, 3′-exo-bicamphor (1).

bicamphor - chiral ligand - methylenation-hydroboration-oxidation - cyclic sulfate - phosphine

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