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American Chemical Society, Journal of Organic Chemistry, 23(72), p. 8904-8909, 2007

DOI: 10.1021/jo7018784

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Complementary stereocontrolled approaches to 2-pyrrolidinones bearing a vicinal amino diol subunit with three continuous chiral centers: A formal asymmetric synthesis of (-)-detoxinine

Journal article published in 2007 by Xiang Zhou, 黄培强, Wen-Jun Liu, Jian-Liang Ye, Pei-Qiang Huang ORCID
This paper was not found in any repository, but could be made available legally by the author.
This paper was not found in any repository, but could be made available legally by the author.

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Abstract

[GRAPHICS] We report herein two stereocomplementary approaches to erythro/trans and threo/cis vicinal amino diol subunits containing 2-pyrrolidinones (9 and 10) starting from the known enamides 7, easily available from malimides. The first approach consists of an epoxidation-reductive dehydroxylation procedure, and the second one is based on hydroboration-oxidation reactions. Using the second method, a formal asymmetric synthesis of (-)-detoxinine was achieved.