(5 S)-1,3-Diaza-2-imino-3-phenylbicyclo[3.3.0]octane: first example of guanidine based in situ recyclable chiral catalytic source for borane-mediated asymmetric reduction of prochiral ketones

(5 S)-1,3-Diaza-2-imino-3-phenylbicyclo[3.3.0]octane has been synthesized and successfully employed, for the first time, as a chiral catalytic source for the borane-mediated asymmetric reduction of prochiral α-halo ketones to provide the corresponding secondary alcohols in high enantiomeric purity....

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Bibliographic Details
Published in:Tetrahedron: asymmetry 2006-04, Vol.17 (7), p.1036-1040
Main Authors: Basavaiah, Deevi, Venkateswara Rao, Kalapala, Sekhara Reddy, Bhavanam
Format: Article
Language:English
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Summary:(5 S)-1,3-Diaza-2-imino-3-phenylbicyclo[3.3.0]octane has been synthesized and successfully employed, for the first time, as a chiral catalytic source for the borane-mediated asymmetric reduction of prochiral α-halo ketones to provide the corresponding secondary alcohols in high enantiomeric purity. The potential of this guanidine as an in situ recyclable chiral catalytic source for the borane-mediated chiral reduction processes has also been demonstrated.
ISSN:0957-4166
1362-511X
DOI:10.1016/j.tetasy.2006.03.020