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

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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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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