Enantioselective synthesis of beta-amino acids. Part 9: Preparation of enantiopure alpha,alpha-disubstituted beta-amino acids from 1-benzoyl-2(S)-tert-butyl-3-methylperhydropyrimidin-4-one

Juaristi E.; Ramirez-Quiros Y.; Balderas M.

首页> 外文期刊>Tetrahedron, Asymmetry: The International Journal for Repid Publication on all Aspects of Asymmetry in Orgainc, Inorganic, Organometallic, Physical and Bio-Organic Chemistry >Enantioselective synthesis of beta-amino acids. Part 9: Preparation of enantiopure alpha,alpha-disubstituted beta-amino acids from 1-benzoyl-2(S)-tert-butyl-3-methylperhydropyrimidin-4-one

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Enantioselective synthesis of beta-amino acids. Part 9: Preparation of enantiopure alpha,alpha-disubstituted beta-amino acids from 1-benzoyl-2(S)-tert-butyl-3-methylperhydropyrimidin-4-one

机译：β-氨基酸的对映选择性合成。第9部分：由1-苯甲酰基-2（S）-叔丁基-3-甲基全氢嘧啶-4-酮制备对映体纯的α，α-二取代的β-氨基酸

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Double alkylation of enantiopure N,N-acetal pyrimidinone (S)-1, a masked chiral derivative of beta-alanine prepared from (S)-asparagine, proceeds with high stereoselectivity to give C(5) disubstituted adducts (2S,5R)-6, (2S,5S)-6, (2S,5R)-7, and (2S,5S)-7. Acid hydrolysis of these derivatives affords enantiopure alpha,alpha-dialkylated beta-amino acids (R)-8, (S)-8, (R)-9, and (S)-9 in very good yields. (C) 1998 Elsevier Science Ltd. All rights reserved. [References: 31]

机译：对映纯N，N-乙缩醛嘧啶酮（S）-1（由（S）-天冬酰胺制备的β-丙氨酸的掩蔽手性衍生物）的双烷基化以高立体选择性进行，得到C（5）二取代的加合物（2S，5R）- 6，（2S，5S）-6，（2S，5R）-7和（2S，5S）-7。这些衍生物的酸水解以非常好的收率提供对映体纯的α，α-二烷基化的β-氨基酸（R）-8，（S）-8，（R）-9和（S）-9。（C）1998 Elsevier ScienceLtd。保留所有权利。 [参考：31]

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《Tetrahedron, Asymmetry: The International Journal for Repid Publication on all Aspects of Asymmetry in Orgainc, Inorganic, Organometallic, Physical and Bio-Organic Chemistry》 |1998年第21期|共8页
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Juaristi E.; Ramirez-Quiros Y.; Balderas M.;
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1. Enantioselective synthesis of beta-amino acids. Part 9: Preparation of enantiopure alpha,alpha-disubstituted beta-amino acids from 1-benzoyl-2(S)-tert-butyl-3-methylperhydropyrimidin-4-one [J] . Juaristi E., Ramirez-Quiros Y., Balderas M. Tetrahedron, Asymmetry: The International Journal for Repid Publication on all Aspects of Asymmetry in Orgainc, Inorganic, Organometallic, Physical and Bio-Organic Chemistry . 1998,第21期

机译：β-氨基酸的对映选择性合成。第9部分：由1-苯甲酰基-2（S）-叔丁基-3-甲基全氢嘧啶-4-酮制备对映体纯的α，α-二取代的β-氨基酸
2. Enantioselective syntheses of beta-amino acids: Part 15. Diastereoselective electrophilic amination of chiral 1-benzoyl-2,3,5,6-tetrahydro-3-methyl-2-(1-methylethyl)pyrimidin-4(1H)-one for the asymmetric syntheses of alpha-substituted alpha,beta-diam [J] . Castellanos E, Reyes-Rangel G, Juaristi E Helvetica chimica acta . 2004,第4期

机译：β-氨基酸的对映选择性合成：第15部分。手性1-苯甲酰基-2,3,5,6-四氢-3-甲基-2-（1-甲基乙基）嘧啶-4（1H）-的非对映选择性亲电胺化反应α-取代的α，β-二胺的不对称合成
3. ENANTIOSELECTIVE SYNTHESIS OF BETA-AMINO ACIDS .6. HIGH 1,2-STEREOINDUCTION IN THE PREPARATION OF ENANTIOPURE 2(R)-HYDROXY-3(R)-N-BENZOYLAMINO-3-PHENYLPROPIONIC ACID (LIKE STEREOISOMER OF TAXOLS SIDE CHAIN) [J] . Escalante J., Juaristi E. Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry . 1995,第25期

机译：对氨基苯甲酸的对映选择性合成.6。制备对映体2（R）-羟基-3（R）-N-苯甲酰氨基-3-苯基丙酸的高1,2-立体诱导作用（类似于TAXOLS侧链的立体异构体）
4. Synthesis and conformational study of(Bin)n and(beta 2,2-Bin)n homopeptides based on atropoisomeric alpha-and beta-amino acids derived from 1,1'-binaphthyl [C] . Anne Gaucher, Laurence Dutot, Karen Wright International Peptide Symposium;European Peptide Symposium . 2005

机译：基于阿托异构体α-β-氨基酸的（Bin）N和（β2,2-Zin）N和（Beta 2,2-Zin）N和（β2,2-Zin）N蛋白肽的合成和构象研究衍生自1,1'-二氯基苯
5. Stereoselective formation of all carbon quaternary centers: Synthesis of alpha,alpha-disubstituted beta-amino carbonyl compounds via the Mannich reaction and total synthesis of (-)-puraquinonic acid. [D] . Tiong, Erica Anne. 2011

机译：所有碳四元中心的立体选择性形成：通过曼尼希反应合成α，α-二取代的β-氨基羰基化合物，以及（-）-嘌呤奎尼酸的全合成。
6. Transaminases for the synthesis of enantiopure beta-amino acids [O] . Jens Rudat, Birgit R Brucher, Christoph Syldatk 2012

机译：转氨酶用于合成对映纯的β-氨基酸
7. Enantioselective hydrogenation of alpha-aminomethylacrylates containing a free N-H group for the synthesis of beta-amino acid derivatives [O] . Qiu, L, Prashad, M, Hu, B, 2007

机译：含游离N-H基团的α-氨基甲基丙烯酸酯的对映选择性氢化，用于合成β-氨基酸衍生物

Enantioselective synthesis of beta-amino acids. Part 9: Preparation of enantiopure alpha,alpha-disubstituted beta-amino acids from 1-benzoyl-2(S)-tert-butyl-3-methylperhydropyrimidin-4-one

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