Sulfinyl group as an intramolecular nucleophile: synthesis of bromohydrins from beta-methyl-gamma,delta-unsaturated sulfoxides with high 1,2-asymmetric induction |
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| Authors: | Raghavan Sadagopan Reddy S Ramakrishna Tony K A Kumar Ch Naveen Varma Ashok K Nangia Ashwini |
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| Institution: | Organic Division I, Indian Institute of Chemical Technology, Hyderabad 500 007, India. purush101@yahoo.com |
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| Abstract: | Bromohydrins have been prepared from beta-methyl-gamma,delta-unsaturated sulfoxides with high regio- and stereoselectivity. The reaction proceeds via neighboring group participation of the sulfinyl moiety with inversion of sulfoxide configuration as proven by an (18)O labeling study and X-ray crystallography. |
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