Highly stereoselective chlorination of β-substituted cyclic alcohols using PPh3-NCS: Factors that control the stereoselectivity

E. A. Jaseer; Ajay B. Naidu; Sreehari S. Kumar; R. Koteshwar Rao; Krishna G. Thakur; G. Sekar

doi:10.1039/b614512d

Highly stereoselective chlorination of β-substituted cyclic alcohols using PPh₃-NCS: Factors that control the stereoselectivity

E. A. Jaseer
, Ajay B. Naidu
, Sreehari S. Kumar
, R. Koteshwar Rao
, Krishna G. Thakur
, G. Sekar^*

^*Corresponding author for this work

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

15 Scopus citations

Abstract

A variety of trans-β-substituted cyclic alcohols were stereoselectively chlorinated to either the corresponding cis-chloride or trans-chloride (inversion or retention of configuration) with good to excellent yields; the stereochemical outcome is determined by the size of the ring and the nature of the β-substituents, especially the electronegativity of the substituted atom.

Original language	English
Pages (from-to)	867-869
Number of pages	3
Journal	Chemical Communications
Issue number	8
DOIs	https://doi.org/10.1039/b614512d
State	Published - 2007
Externally published	Yes

ASJC Scopus subject areas

Electronic, Optical and Magnetic Materials
Catalysis
Ceramics and Composites
General Chemistry
Surfaces, Coatings and Films
Metals and Alloys
Materials Chemistry

Access to Document

10.1039/b614512d

Cite this

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title = "Highly stereoselective chlorination of β-substituted cyclic alcohols using PPh3-NCS: Factors that control the stereoselectivity",

abstract = "A variety of trans-β-substituted cyclic alcohols were stereoselectively chlorinated to either the corresponding cis-chloride or trans-chloride (inversion or retention of configuration) with good to excellent yields; the stereochemical outcome is determined by the size of the ring and the nature of the β-substituents, especially the electronegativity of the substituted atom.",

author = "Jaseer, \{E. A.\} and Naidu, \{Ajay B.\} and Kumar, \{Sreehari S.\} and Rao, \{R. Koteshwar\} and Thakur, \{Krishna G.\} and G. Sekar",

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language = "English",

pages = "867--869",

journal = "Chemical Communications",

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T1 - Highly stereoselective chlorination of β-substituted cyclic alcohols using PPh3-NCS

T2 - Factors that control the stereoselectivity

AU - Jaseer, E. A.

AU - Naidu, Ajay B.

AU - Kumar, Sreehari S.

AU - Rao, R. Koteshwar

AU - Thakur, Krishna G.

AU - Sekar, G.

PY - 2007

Y1 - 2007

N2 - A variety of trans-β-substituted cyclic alcohols were stereoselectively chlorinated to either the corresponding cis-chloride or trans-chloride (inversion or retention of configuration) with good to excellent yields; the stereochemical outcome is determined by the size of the ring and the nature of the β-substituents, especially the electronegativity of the substituted atom.

AB - A variety of trans-β-substituted cyclic alcohols were stereoselectively chlorinated to either the corresponding cis-chloride or trans-chloride (inversion or retention of configuration) with good to excellent yields; the stereochemical outcome is determined by the size of the ring and the nature of the β-substituents, especially the electronegativity of the substituted atom.

UR - https://www.scopus.com/pages/publications/33847050798

U2 - 10.1039/b614512d

DO - 10.1039/b614512d

M3 - Article

AN - SCOPUS:33847050798

SN - 1359-7345

SP - 867

EP - 869

JO - Chemical Communications

JF - Chemical Communications

IS - 8