Studies on the synthesis of (2S,3R)-3-hydroxy-3-methylproline via C2-N bond formation |
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Authors: | Shen Jun-Wei Qin Dong-Guang Zhang Hong-Wang Yao Zhu-Jun |
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Institution: | State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, China. |
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Abstract: | A new efficient synthesis of (2S,3R)-3-hydroxy-3-methylproline (3) is reported. During the course of a recent study on the Lewis acid promoted intramolecular opening of an epoxide by a carbamate NH, a highly concerted rearrangement was unexpectedly observed. Further investigations of substrate generality show that delta-carbamate-alpha,beta-epoxide esters commonly underwent similar rearrangements with the aid of Lewis acids. Retrosynthetic analysis of such a C(2)-N disconnection can lead to an efficient synthesis of (2S,3R)-3-hydroxy-3-methylproline (3) in high enantio purity. Stereochemistries were established by a Sharpless asymmetric dihydroxylation and a diastereoselective reductive amination. |
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