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

E. A. Jaseer; Govindasamy Sekar

doi:10.1016/j.tetasy.2010.04.011

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

E. A. Jaseer
, Govindasamy Sekar^*

^*Corresponding author for this work

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

5 Scopus citations

Abstract

A series of optically active cyclic trans-β-amido alcohols were obtained by the non-enzymatic kinetic resolution of the corresponding racemic amido alcohols using commercially available (S)-BINAP and NCS by S_N2 halogenation of the hydroxy group. The product, cis-β-amido chloride, was also obtained in optically active form with an inversion of stereochemistry.

Original language	English
Pages (from-to)	780-785
Number of pages	6
Journal	Tetrahedron Asymmetry
Volume	21
Issue number	7
DOIs	https://doi.org/10.1016/j.tetasy.2010.04.011
State	Published - 21 Apr 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. thanks CSIR, New Delhi, for fellowship. We thank DST, New Delhi, for funding towards 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.2010.04.011

Cite this

@article{c05b3c6315844838bcdbe184fd8669b2,

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

abstract = "A series of optically active cyclic trans-β-amido alcohols were obtained by the non-enzymatic kinetic resolution of the corresponding racemic amido alcohols using commercially available (S)-BINAP and NCS by SN2 halogenation of the hydroxy group. The product, cis-β-amido chloride, was also obtained in optically active form with an inversion of stereochemistry.",

author = "Jaseer, \{E. A.\} 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. thanks CSIR, New Delhi, for fellowship. We thank DST, New Delhi, for funding towards 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",

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doi = "10.1016/j.tetasy.2010.04.011",

language = "English",

volume = "21",

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T1 - Halogenative kinetic resolution of β-amido alcohols

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

AU - Jaseer, E. A.

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. thanks CSIR, New Delhi, for fellowship. We thank DST, New Delhi, for funding towards 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 - 2010/4/21

Y1 - 2010/4/21

N2 - A series of optically active cyclic trans-β-amido alcohols were obtained by the non-enzymatic kinetic resolution of the corresponding racemic amido alcohols using commercially available (S)-BINAP and NCS by SN2 halogenation of the hydroxy group. The product, cis-β-amido chloride, was also obtained in optically active form with an inversion of stereochemistry.

AB - A series of optically active cyclic trans-β-amido alcohols were obtained by the non-enzymatic kinetic resolution of the corresponding racemic amido alcohols using commercially available (S)-BINAP and NCS by SN2 halogenation of the hydroxy group. The product, cis-β-amido chloride, was also obtained in optically active form with an inversion of stereochemistry.

UR - https://www.scopus.com/pages/publications/77956189284

U2 - 10.1016/j.tetasy.2010.04.011

DO - 10.1016/j.tetasy.2010.04.011

M3 - Article

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SN - 0957-4166

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SP - 780

EP - 785

JO - Tetrahedron Asymmetry

JF - Tetrahedron Asymmetry

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ER -