An Enantioselective Synthesis of (+)-Polyoxamic Acid via Phase-Transfer Catalytic Conjugate Addition and Asymmetric Dihydroxylation
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Title
- An Enantioselective Synthesis of (+)-Polyoxamic Acid via Phase-Transfer Catalytic Conjugate Addition and Asymmetric Dihydroxylation
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Author(s)
- Lee, Yeon-Ju; Park, Yohan; Kim, Mi-hyun; Jew, Sang-sup; Park, Hyeung-geun
- KIOST Author(s)
- Lee, Yeon Ju(이연주)
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Alternative Author(s)
- 이연주
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Publication Year
- 2011-01-21
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Abstract
- A new enantioselective synthetic method of (+)-polyoxamic acid is reported. (+)-Polyoxamic acid could be obtained in 7 steps with 46% overall yield from diphenylmethyl-glycineimine tert-butyl ester via an enantioselective phase-transfer conjugate addition (99% yield, 96% ee) and an asymmetric dihydroxylation (98% yield, 94% de) as the key reactions.
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ISSN
- 0022-3263
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URI
- https://sciwatch.kiost.ac.kr/handle/2020.kiost/3891
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DOI
- 10.1021/jo102272h
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Bibliographic Citation
- JOURNAL OF ORGANIC CHEMISTRY, v.76, no.2, pp.740 - 743, 2011
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Publisher
- AMER CHEMICAL SOC
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Subject
- ALPHA-AMINO-ACIDS; POLYOXAMIC ACID; BIOLOGICAL-ACTIVITY; STEREOSELECTIVE-SYNTHESIS; 3,4-DIEPIPOLYOXAMIC ACID; EFFICIENT SYNTHESIS; ALKYLATION; SERINE; AGENTS; ROUTE
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Type
- Article
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Language
- English
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Document Type
- Article
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