Highly stereoselective chlorination of beta-substituted cyclic alcohols using PPh3-NCS: factors that control the stereoselectivity |
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| Authors: | Jaseer E A Naidu Ajay B Kumar Sreehari S Rao R Koteshwar Thakur Krishna G Sekar G |
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| Affiliation: | Department of Chemistry, Indian Institute of Technology Madras, Chennai, Tamil Nadu, 600 036, India. |
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| Abstract: | A variety of trans-beta-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 beta-substituents, especially the electronegativity of the substituted atom. |
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