Enantioselective deprotonation of protected 4-hydroxycyclohexanones

doi:10.1139/V94-214

Paper

Enantioselective deprotonation of protected 4-hydroxycyclohexanones

Published Jul 1, 1994 · M. Majewski, J. Mackinnon

Canadian Journal of Chemistry

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24

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Abstract

A series of derivatives of 4-hydroxycyclohexanone (1a–g) with the hydroxy group protected as a silyl ether (1a, b), ether (1d, g), an acetal (1c), or an ester (1e, f) were deprotonated with chiral, optically pure, lithium amides 3–9. The resulting non-racemic enolates were trapped as enol acetates. The enantioselectivity of deprotonation was up to 74% ee.

Study Snapshot

Enantioselective deprotonation of protected 4-hydroxycyclohexanones with chiral lithium amides can produce non-racemic enolates with up to 74% ee.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Enantioselective deprotonation of protected 4-hydroxycyclohexanones

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References

Introduction to Stereochemistry and Conformational Analysis

Chiral organic synthesis, conformational analysis, and control of stereochemistry are crucial for understanding and analyzing complex organic compounds.

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