New cyclohexyl-based chiral auxiliaries: enantioselective synthesis of α-hydroxy acids

Basavaiah, Deevi ; Krishna, Peddinti Rama (1995) New cyclohexyl-based chiral auxiliaries: enantioselective synthesis of α-hydroxy acids Tetrahedron, 51 (44). pp. 12169-12178. ISSN 0040-4020

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Official URL: http://linkinghub.elsevier.com/retrieve/pii/004040...

Related URL: http://dx.doi.org/10.1016/0040-4020(95)00771-Y

Abstract

(1R,2R)-2-(4-tert-Butylphenoxy)cyclohexan-1-ol (5) and (1R,2R)-2-(4-phenylphenoxy)cyclohexan-1-ol (6) have been used for the first time as chiral auxiliaries. Addition of alkylzinc chlorides to the corresponding glyoxylates 5a, 6a, after hydrolysis, provided (R)-α-hydroxy acids in high optical purities.

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