Reversal of facial selectivity in the kinetic resolution of olefin via asymmetric dihydroxylation (AD) reaction: Synthesis of optically active (-)-mintlactone and (+)-isomintlactone by AD reaction from intrinsically disfavoured diastereoface of alkene | Health & Environmental Research Online (HERO)

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HERO ID

7951757

Reference Type

Journal Article

Title

Reversal of facial selectivity in the kinetic resolution of olefin via asymmetric dihydroxylation (AD) reaction: Synthesis of optically active (-)-mintlactone and (+)-isomintlactone by AD reaction from intrinsically disfavoured diastereoface of alkene

Author(s)

Lohray, BB; Nandanan, E; Bhushan, V

Year

1997

Is Peer Reviewed?

Journal

Indian Journal of Chemistry. Section B
ISSN: 0376-4699
EISSN: 0975-0983

Volume

Issue

Page Numbers

226-231

Language

English

Web of Science Id

WOS:A1997XB55600005

Abstract

Reversal of diastereofacial selectivity in the kinetic resolution of 4-methyl-1-(carbethoxymethylene)cyclohexane 6 has been observed during asymmetric dihydroxylation reaction using different chiral auxiliaries. The AD reaction of 6 proceeds from a favoured diastereoface when DHQD2-TP or DHQD-CLB are used, whereas unfavoured diastereofacial selection is observed when DHQD2-PHAL is used as chiral auxiliary. Similarly, AD reaction of ethyl α-(4-methylcyclohex-lene)propionate 5 proceeds via unfavoured diastereoface; resulting in axial dihydroxylation, to afford (-)-mintlactone 1 and (+)-isomintlactone 2.