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Synthesis 1999; 1999(5): 835-838
DOI: 10.1055/s-1999-3478
DOI: 10.1055/s-1999-3478
paper
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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
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Publikationsdatum:
31. Dezember 1999 (online)
![](https://www.thieme-connect.de/media/synthesis/199905/lookinside/thumbnails/10.1055-s-1999-3478-1.jpg)
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