Efficient kinetic resolution of 2-benzenesulfonylcyclopentanone derivatives

Anita R. Maguire; Leonard L. Kelleher; George Ferguson

doi:10.1016/1381-1177(95)00019-4

Efficient kinetic resolution of 2-benzenesulfonylcyclopentanone derivatives

Anita R. Maguire
, Leonard L. Kelleher
, George Ferguson

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

Abstract

Efficient kinetic resolution of 2-benzenesulfonylcyclopentanones 1, bearing 3-alkyl, 3-aryl, or 3-benzyl substituents, has been achieved by bakers' yeast mediated reduction. With the unsubstituted 2-benzenesulfonylcyclopentanone 1a, efficient asymmetric reduction to form (1S,2R)-cis-2-benzenesulfonylcyclopentanol 2a is observed under the same conditions. Excellent enantioselectivities (up to > 95% ee) are obtained.

Original language	English
Pages (from-to)	115-126
Number of pages	12
Journal	Journal of Molecular Catalysis - B Enzymatic
Volume	1
Issue number	3-6
DOIs	https://doi.org/10.1016/1381-1177(95)00019-4
Publication status	Published - Jun 1996

Keywords

Bakers' yeast
Chiral derivatives
Cyclopentane derivatives
Kinetic resolution
Reduction
β-Keto sulfones

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10.1016/1381-1177(95)00019-4

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title = "Efficient kinetic resolution of 2-benzenesulfonylcyclopentanone derivatives",

abstract = "Efficient kinetic resolution of 2-benzenesulfonylcyclopentanones 1, bearing 3-alkyl, 3-aryl, or 3-benzyl substituents, has been achieved by bakers' yeast mediated reduction. With the unsubstituted 2-benzenesulfonylcyclopentanone 1a, efficient asymmetric reduction to form (1S,2R)-cis-2-benzenesulfonylcyclopentanol 2a is observed under the same conditions. Excellent enantioselectivities (up to > 95\% ee) are obtained.",

keywords = "Bakers' yeast, Chiral derivatives, Cyclopentane derivatives, Kinetic resolution, Reduction, β-Keto sulfones",

author = "Maguire, \{Anita R.\} and Kelleher, \{Leonard L.\} and George Ferguson",

year = "1996",

month = jun,

doi = "10.1016/1381-1177(95)00019-4",

language = "English",

volume = "1",

pages = "115--126",

journal = "Journal of Molecular Catalysis - B Enzymatic",

issn = "1381-1177",

publisher = "Elsevier",

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}

TY - JOUR

T1 - Efficient kinetic resolution of 2-benzenesulfonylcyclopentanone derivatives

AU - Maguire, Anita R.

AU - Kelleher, Leonard L.

AU - Ferguson, George

PY - 1996/6

Y1 - 1996/6

N2 - Efficient kinetic resolution of 2-benzenesulfonylcyclopentanones 1, bearing 3-alkyl, 3-aryl, or 3-benzyl substituents, has been achieved by bakers' yeast mediated reduction. With the unsubstituted 2-benzenesulfonylcyclopentanone 1a, efficient asymmetric reduction to form (1S,2R)-cis-2-benzenesulfonylcyclopentanol 2a is observed under the same conditions. Excellent enantioselectivities (up to > 95% ee) are obtained.

AB - Efficient kinetic resolution of 2-benzenesulfonylcyclopentanones 1, bearing 3-alkyl, 3-aryl, or 3-benzyl substituents, has been achieved by bakers' yeast mediated reduction. With the unsubstituted 2-benzenesulfonylcyclopentanone 1a, efficient asymmetric reduction to form (1S,2R)-cis-2-benzenesulfonylcyclopentanol 2a is observed under the same conditions. Excellent enantioselectivities (up to > 95% ee) are obtained.

KW - Bakers' yeast

KW - Chiral derivatives

KW - Cyclopentane derivatives

KW - Kinetic resolution

KW - Reduction

KW - β-Keto sulfones

UR - https://www.scopus.com/pages/publications/0030568609

U2 - 10.1016/1381-1177(95)00019-4

DO - 10.1016/1381-1177(95)00019-4

M3 - Article

AN - SCOPUS:0030568609

SN - 1381-1177

VL - 1

SP - 115

EP - 126

JO - Journal of Molecular Catalysis - B Enzymatic

JF - Journal of Molecular Catalysis - B Enzymatic

IS - 3-6

ER -

Efficient kinetic resolution of 2-benzenesulfonylcyclopentanone derivatives

Abstract

Keywords

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