Raghavan, Sadagopan ; Reddy, S. Ramakrishna ; Tony, K. A. ; Kumar, Ch. Naveen ; Varma, Ashok K. ; Nangia, Ashwini (2002) Sulfinyl group as an intramolecular nucleophile: synthesis of bromohydrins from β -methyl-γ,δ-unsaturated sulfoxides with high 1,2-asymmetric induction† Journal of Organic Chemistry, 67 (16). pp. 5838-5841. ISSN 0022-3263
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Official URL: http://pubs.acs.org/doi/abs/10.1021/jo015921m?prev...
Related URL: http://dx.doi.org/10.1021/jo015921m
Abstract
Bromohydrins have been prepared from β-methyl-γ,δ-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 18O labeling study and X-ray crystallography.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to American Chemical Society. |
| ID Code: | 24598 |
| Deposited On: | 29 Nov 2010 08:53 |
| Last Modified: | 04 Mar 2011 05:42 |
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