Enantioselective deprotonation of cyclohexene oxide to (R)-2-cyclohexen-1-ol

Bhuniya, Debnath ; Singh, Vinod K. (1994) Enantioselective deprotonation of cyclohexene oxide to (R)-2-cyclohexen-1-ol Synthetic Communications, 24 (10). pp. 1475-1481. ISSN 0039-7911

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Official URL: http://www.tandfonline.com/doi/abs/10.1080/0039791...

Related URL: http://dx.doi.org/10.1080/00397919408011752

Abstract

The reaction of cyclohexene oxide with homochiral lithium amides, prepared from (S)-phenylglycine and (S)-valine has been studied and (R)-2-cyclohexen-1-ol 3 was prepared in a maximum of 72% ee. The optical purity was determined by 1H NMR measurement of the α-methoxy-α-(trifluoromethyl)phenyl acetic acid (MTPA) derivative of the corresponding alcohol.

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