Parallel kinetic resolution of tert-butyl (RS)-6-alkyl-cyclohex-1-ene-carboxylates for the asymmetric synthesis of 6-alkyl-substituted cishexacin derivatives

Stephen G. Davies; Matthew J. Durbin; Scott J. S. Hartman; Ai Matsuno; Paul M. Roberts; Angela J. Russell; Andrew D. Smith; James E. Thomson; Steven M. Toms

doi:10.1016/j.tetasy.2008.11.019

Parallel kinetic resolution of tert-butyl (RS)-6-alkyl-cyclohex-1-ene-carboxylates for the asymmetric synthesis of 6-alkyl-substituted cishexacin derivatives

Stephen G. Davies, Matthew J. Durbin, Scott J. S. Hartman, Ai Matsuno, Paul M. Roberts, Angela J. Russell, Andrew D. Smith, James E. Thomson, Steven M. Toms

Research output: Contribution to journal › Article › peer-review

33 Citations (Scopus)

Abstract

Excellent levels of enantiorecognition are displayed by tert-butyl (RS)-6-n-alkyl-cyclohex-1-ene-carboxylates in mutual kinetic resolutions with lithium (RS)-N-benzyl]-N-(alpha-methylbenzyl)amide. Therefore a 50:50 pseudoenantiomeric mixture of lithium (S)-N-benzyl-N-(alpha-methylbenzyl)amide and lithium (R)-N-3,4-dimethoxybenzyl-N-(alpha-methylbenzyl)amide allows their efficient parallel kinetic resolution, affording differentially protected 6-n-alkyl-cishexacin derivatives in high yield and >95% de. N-Debenzylation and ester hydrolysis give access to the corresponding homochiral 6-n-alkyl-substituted cishexacin derivatives. (C) 2008 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	2870-2881
Number of pages	12
Journal	Tetrahedron: Asymmetry
Volume	19
Issue number	24
DOIs	https://doi.org/10.1016/j.tetasy.2008.11.019
Publication status	Published - 12 Dec 2008

Keywords

DIASTEREOSELECTIVE CONJUGATE ADDITION
HELICAL SECONDARY STRUCTURE
HOMOCHIRAL LITHIUM AMIDES
BETA-PEPTIDE
GRIGNARD-REAGENTS
ACIDS
3-ALKYL-CISPENTACIN
STEREOCHEMISTRY
HEXAPEPTIDE
PROTONATION

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10.1016/j.tetasy.2008.11.019

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Davies, S. G., Durbin, M. J., Hartman, S. J. S., Matsuno, A., Roberts, P. M., Russell, A. J., Smith, A. D., Thomson, J. E., & Toms, S. M. (2008). Parallel kinetic resolution of tert-butyl (RS)-6-alkyl-cyclohex-1-ene-carboxylates for the asymmetric synthesis of 6-alkyl-substituted cishexacin derivatives. Tetrahedron: Asymmetry, 19(24), 2870-2881. https://doi.org/10.1016/j.tetasy.2008.11.019

@article{d94c966bf0d1493e9f165933269d0c8e,

title = "Parallel kinetic resolution of tert-butyl (RS)-6-alkyl-cyclohex-1-ene-carboxylates for the asymmetric synthesis of 6-alkyl-substituted cishexacin derivatives",

abstract = "Excellent levels of enantiorecognition are displayed by tert-butyl (RS)-6-n-alkyl-cyclohex-1-ene-carboxylates in mutual kinetic resolutions with lithium (RS)-N-benzyl]-N-(alpha-methylbenzyl)amide. Therefore a 50:50 pseudoenantiomeric mixture of lithium (S)-N-benzyl-N-(alpha-methylbenzyl)amide and lithium (R)-N-3,4-dimethoxybenzyl-N-(alpha-methylbenzyl)amide allows their efficient parallel kinetic resolution, affording differentially protected 6-n-alkyl-cishexacin derivatives in high yield and >95% de. N-Debenzylation and ester hydrolysis give access to the corresponding homochiral 6-n-alkyl-substituted cishexacin derivatives. (C) 2008 Elsevier Ltd. All rights reserved.",

keywords = "DIASTEREOSELECTIVE CONJUGATE ADDITION, HELICAL SECONDARY STRUCTURE, HOMOCHIRAL LITHIUM AMIDES, BETA-PEPTIDE, GRIGNARD-REAGENTS, ACIDS, 3-ALKYL-CISPENTACIN, STEREOCHEMISTRY, HEXAPEPTIDE, PROTONATION",

author = "Davies, {Stephen G.} and Durbin, {Matthew J.} and Hartman, {Scott J. S.} and Ai Matsuno and Roberts, {Paul M.} and Russell, {Angela J.} and Smith, {Andrew D.} and Thomson, {James E.} and Toms, {Steven M.}",

year = "2008",

month = dec,

day = "12",

doi = "10.1016/j.tetasy.2008.11.019",

language = "English",

volume = "19",

pages = "2870--2881",

journal = "Tetrahedron: Asymmetry",

issn = "0957-4166",

publisher = "Elsevier",

number = "24",

}

Davies, SG, Durbin, MJ, Hartman, SJS, Matsuno, A, Roberts, PM, Russell, AJ, Smith, AD, Thomson, JE & Toms, SM 2008, 'Parallel kinetic resolution of tert-butyl (RS)-6-alkyl-cyclohex-1-ene-carboxylates for the asymmetric synthesis of 6-alkyl-substituted cishexacin derivatives', Tetrahedron: Asymmetry, vol. 19, no. 24, pp. 2870-2881. https://doi.org/10.1016/j.tetasy.2008.11.019

TY - JOUR

T1 - Parallel kinetic resolution of tert-butyl (RS)-6-alkyl-cyclohex-1-ene-carboxylates for the asymmetric synthesis of 6-alkyl-substituted cishexacin derivatives

AU - Davies, Stephen G.

AU - Durbin, Matthew J.

AU - Hartman, Scott J. S.

AU - Matsuno, Ai

AU - Roberts, Paul M.

AU - Russell, Angela J.

AU - Smith, Andrew D.

AU - Thomson, James E.

AU - Toms, Steven M.

PY - 2008/12/12

Y1 - 2008/12/12

N2 - Excellent levels of enantiorecognition are displayed by tert-butyl (RS)-6-n-alkyl-cyclohex-1-ene-carboxylates in mutual kinetic resolutions with lithium (RS)-N-benzyl]-N-(alpha-methylbenzyl)amide. Therefore a 50:50 pseudoenantiomeric mixture of lithium (S)-N-benzyl-N-(alpha-methylbenzyl)amide and lithium (R)-N-3,4-dimethoxybenzyl-N-(alpha-methylbenzyl)amide allows their efficient parallel kinetic resolution, affording differentially protected 6-n-alkyl-cishexacin derivatives in high yield and >95% de. N-Debenzylation and ester hydrolysis give access to the corresponding homochiral 6-n-alkyl-substituted cishexacin derivatives. (C) 2008 Elsevier Ltd. All rights reserved.

AB - Excellent levels of enantiorecognition are displayed by tert-butyl (RS)-6-n-alkyl-cyclohex-1-ene-carboxylates in mutual kinetic resolutions with lithium (RS)-N-benzyl]-N-(alpha-methylbenzyl)amide. Therefore a 50:50 pseudoenantiomeric mixture of lithium (S)-N-benzyl-N-(alpha-methylbenzyl)amide and lithium (R)-N-3,4-dimethoxybenzyl-N-(alpha-methylbenzyl)amide allows their efficient parallel kinetic resolution, affording differentially protected 6-n-alkyl-cishexacin derivatives in high yield and >95% de. N-Debenzylation and ester hydrolysis give access to the corresponding homochiral 6-n-alkyl-substituted cishexacin derivatives. (C) 2008 Elsevier Ltd. All rights reserved.

KW - DIASTEREOSELECTIVE CONJUGATE ADDITION

KW - HELICAL SECONDARY STRUCTURE

KW - HOMOCHIRAL LITHIUM AMIDES

KW - BETA-PEPTIDE

KW - GRIGNARD-REAGENTS

KW - ACIDS

KW - 3-ALKYL-CISPENTACIN

KW - STEREOCHEMISTRY

KW - HEXAPEPTIDE

KW - PROTONATION

U2 - 10.1016/j.tetasy.2008.11.019

DO - 10.1016/j.tetasy.2008.11.019

M3 - Article

SN - 0957-4166

VL - 19

SP - 2870

EP - 2881

JO - Tetrahedron: Asymmetry

JF - Tetrahedron: Asymmetry

IS - 24

ER -

Parallel kinetic resolution of tert-butyl (RS)-6-alkyl-cyclohex-1-ene-carboxylates for the asymmetric synthesis of 6-alkyl-substituted cishexacin derivatives

Abstract

Keywords

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