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Highly Enantioselective Phase-Transfer-Catalytic Alkylation of 2-Phenyl-2-oxazoline-4-carboxylic Acid tert-Butyl Ester for the Asymmetric Synthesis of α-Alkyl Serines

Authors

  • Sang-sup Jew Prof.,

    1. Research Institute of Pharmaceutical Sciences and College of Pharmacy, Seoul National University, San 56-1, Shinlim-Dong, Gwanak-Gu, Seoul 151-742, Korea, Fax: (+82) 2-872-9129
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  • Yeon-Ju Lee,

    1. Research Institute of Pharmaceutical Sciences and College of Pharmacy, Seoul National University, San 56-1, Shinlim-Dong, Gwanak-Gu, Seoul 151-742, Korea, Fax: (+82) 2-872-9129
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  • Jihye Lee,

    1. Research Institute of Pharmaceutical Sciences and College of Pharmacy, Seoul National University, San 56-1, Shinlim-Dong, Gwanak-Gu, Seoul 151-742, Korea, Fax: (+82) 2-872-9129
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  • Myoung Joo Kang,

    1. Research Institute of Pharmaceutical Sciences and College of Pharmacy, Seoul National University, San 56-1, Shinlim-Dong, Gwanak-Gu, Seoul 151-742, Korea, Fax: (+82) 2-872-9129
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  • Byeong-Seon Jeong,

    1. Research Institute of Pharmaceutical Sciences and College of Pharmacy, Seoul National University, San 56-1, Shinlim-Dong, Gwanak-Gu, Seoul 151-742, Korea, Fax: (+82) 2-872-9129
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  • Jeong-Hee Lee,

    1. Research Institute of Pharmaceutical Sciences and College of Pharmacy, Seoul National University, San 56-1, Shinlim-Dong, Gwanak-Gu, Seoul 151-742, Korea, Fax: (+82) 2-872-9129
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  • Mi-Sook Yoo,

    1. Research Institute of Pharmaceutical Sciences and College of Pharmacy, Seoul National University, San 56-1, Shinlim-Dong, Gwanak-Gu, Seoul 151-742, Korea, Fax: (+82) 2-872-9129
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  • Mi-Jeong Kim,

    1. Research Institute of Pharmaceutical Sciences and College of Pharmacy, Seoul National University, San 56-1, Shinlim-Dong, Gwanak-Gu, Seoul 151-742, Korea, Fax: (+82) 2-872-9129
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  • Sea-hoon Choi,

    1. Research Institute of Pharmaceutical Sciences and College of Pharmacy, Seoul National University, San 56-1, Shinlim-Dong, Gwanak-Gu, Seoul 151-742, Korea, Fax: (+82) 2-872-9129
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  • Jin-Mo Ku,

    1. Research Institute of Pharmaceutical Sciences and College of Pharmacy, Seoul National University, San 56-1, Shinlim-Dong, Gwanak-Gu, Seoul 151-742, Korea, Fax: (+82) 2-872-9129
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  • Hyeung-geun Park Prof.

    1. Research Institute of Pharmaceutical Sciences and College of Pharmacy, Seoul National University, San 56-1, Shinlim-Dong, Gwanak-Gu, Seoul 151-742, Korea, Fax: (+82) 2-872-9129
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  • This work was supported by a grant (R01-2002-000-0005-0) from the Basic Research Program of the KOSEF (2003).

Abstract

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Eine einfache Synthese der chiralen α-Alkylserine 3 gelingt durch die asymmetrische Alkylierung der Substrate 1 mit Alkylhalogeniden (RX) unter Phasentransferkatalyse (PTC) und die anschließende saure Hydrolyse der Alkylierungsprodukte 2. Die Phenyloxazolin-Einheit steigert die Acidität des Ester-α-Protons und ist zugleich eine hervorragende Schutzgruppe für sowohl die Amino- als auch die Hydroxyfunktion des Serinesters.

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