Halogenative kinetic resolution of β-aryloxy cyclic alcohols: Chiral BINAP-mediated SN2 displacement of hydroxy groups by chlorides with inversion of stereochemistry

E. A. Jaseer; I. Karthikeyan; Govindasamy Sekar

doi:10.1016/j.tetasy.2010.06.034

Halogenative kinetic resolution of β-aryloxy cyclic alcohols: Chiral BINAP-mediated S_N2 displacement of hydroxy groups by chlorides with inversion of stereochemistry

E. A. Jaseer
, I. Karthikeyan
, Govindasamy Sekar^*

^*Corresponding author for this work

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

1 Scopus citations

Abstract

A series of optically active cyclic trans-β-aryloxy alcohols have been obtained by non-enzymatic kinetic resolution of the corresponding racemic aryloxy cyclic alcohols using commercially available (S)-BINAP and NCS by S _N2 halogenation of a hydroxy group. The product, cis-β-aryloxy chlorides, was also obtained in optically active form with inversion of the stereochemistry.

Original language	English
Pages (from-to)	2177-2182
Number of pages	6
Journal	Tetrahedron Asymmetry
Volume	21
Issue number	17
DOIs	https://doi.org/10.1016/j.tetasy.2010.06.034
State	Published - 8 Sep 2010
Externally published	Yes

Bibliographical note

Funding Information:
We thank DST (Project No.: SR/S1/OC-06/2008) and CSIR, New Delhi, for the financial support. E.A.J. and I.K. thank CSIR, New Delhi, for the fellowship. We thank DST, New Delhi, for the funding toward the 400 MHz NMR machine to the Department of Chemistry, IIT-Madras, under the IRPHA scheme and ESI-MS facility under the FIST programme.

ASJC Scopus subject areas

Catalysis
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

Access to Document

10.1016/j.tetasy.2010.06.034

Cite this

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title = "Halogenative kinetic resolution of β-aryloxy cyclic alcohols: Chiral BINAP-mediated SN2 displacement of hydroxy groups by chlorides with inversion of stereochemistry",

abstract = "A series of optically active cyclic trans-β-aryloxy alcohols have been obtained by non-enzymatic kinetic resolution of the corresponding racemic aryloxy cyclic alcohols using commercially available (S)-BINAP and NCS by S N2 halogenation of a hydroxy group. The product, cis-β-aryloxy chlorides, was also obtained in optically active form with inversion of the stereochemistry.",

author = "Jaseer, \{E. A.\} and I. Karthikeyan and Govindasamy Sekar",

note = "Funding Information: We thank DST (Project No.: SR/S1/OC-06/2008) and CSIR, New Delhi, for the financial support. E.A.J. and I.K. thank CSIR, New Delhi, for the fellowship. We thank DST, New Delhi, for the funding toward the 400 MHz NMR machine to the Department of Chemistry, IIT-Madras, under the IRPHA scheme and ESI-MS facility under the FIST programme.",

year = "2010",

month = sep,

day = "8",

doi = "10.1016/j.tetasy.2010.06.034",

language = "English",

volume = "21",

pages = "2177--2182",

journal = "Tetrahedron Asymmetry",

issn = "0957-4166",

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TY - JOUR

T1 - Halogenative kinetic resolution of β-aryloxy cyclic alcohols

T2 - Chiral BINAP-mediated SN2 displacement of hydroxy groups by chlorides with inversion of stereochemistry

AU - Jaseer, E. A.

AU - Karthikeyan, I.

AU - Sekar, Govindasamy

N1 - Funding Information: We thank DST (Project No.: SR/S1/OC-06/2008) and CSIR, New Delhi, for the financial support. E.A.J. and I.K. thank CSIR, New Delhi, for the fellowship. We thank DST, New Delhi, for the funding toward the 400 MHz NMR machine to the Department of Chemistry, IIT-Madras, under the IRPHA scheme and ESI-MS facility under the FIST programme.

PY - 2010/9/8

Y1 - 2010/9/8

N2 - A series of optically active cyclic trans-β-aryloxy alcohols have been obtained by non-enzymatic kinetic resolution of the corresponding racemic aryloxy cyclic alcohols using commercially available (S)-BINAP and NCS by S N2 halogenation of a hydroxy group. The product, cis-β-aryloxy chlorides, was also obtained in optically active form with inversion of the stereochemistry.

AB - A series of optically active cyclic trans-β-aryloxy alcohols have been obtained by non-enzymatic kinetic resolution of the corresponding racemic aryloxy cyclic alcohols using commercially available (S)-BINAP and NCS by S N2 halogenation of a hydroxy group. The product, cis-β-aryloxy chlorides, was also obtained in optically active form with inversion of the stereochemistry.

UR - https://www.scopus.com/pages/publications/77956191229

U2 - 10.1016/j.tetasy.2010.06.034

DO - 10.1016/j.tetasy.2010.06.034

M3 - Article

AN - SCOPUS:77956191229

SN - 0957-4166

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EP - 2182

JO - Tetrahedron Asymmetry

JF - Tetrahedron Asymmetry

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