(5S)-1-Aza-2-imino-3-oxa-4,4-diphenylbicyclo(3.3.0)octane: a novel chiral catalytic source containing the N-(C=NH)-O moiety for the borane-mediated asymmetric reduction of prochiral ketones

Basavaiah, Deevi ; Rao, Kalapala Venkateswara ; Reddy, Bhavanam Sekhara (2007) (5S)-1-Aza-2-imino-3-oxa-4,4-diphenylbicyclo(3.3.0)octane: a novel chiral catalytic source containing the N-(C=NH)-O moiety for the borane-mediated asymmetric reduction of prochiral ketones Tetrahedron: Asymmetry, 18 (8). pp. 963-967. ISSN 0957-4166

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Official URL: http://linkinghub.elsevier.com/retrieve/pii/S09574...

Related URL: http://dx.doi.org/10.1016/j.tetasy.2007.03.017

Abstract

(5S)-1-Aza-2-imino-3-oxa-4,4-diphenylbicyclo(3.3.0)octane, a novel chiral catalytic source containing the N-(C=NH)-O moiety, has been synthesized and successfully utilized, for the first time, as a chiral catalytic source in the borane-mediated asymmetric reduction of prochiral ketones in refluxing toluene, to provide the corresponding secondary alcohols with up to 93% enantiomeric excess.

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