Stereospecific Synthesis of β~3-Amino Acid Derivatives from Propargylic Alcohols: Efficient Solution-Phase Synthesis of Oligopeptides without Coupling Agents

Andrea Temperini; Raffaella Terlizzi; Lorenzo Testaferri; Marcello Tiecco

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Stereospecific Synthesis of β~3-Amino Acid Derivatives from Propargylic Alcohols: Efficient Solution-Phase Synthesis of Oligopeptides without Coupling Agents

机译：从炔丙醇立体定向合成β〜3-氨基酸衍生物：无需偶联剂的寡肽高效液相合成

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A stereospecific synthesis of β~3-amino acids has been accomplished starting from readily available and enantioenriched propargylic alcohols. This conversion can be effected in only three steps by selenium-mediated organic transformations of the carbon–carbon triple bond. This method is especially attractive because the reactive Se-phenyl selenocarboxylate intermediates can be trapped with the amine functionality of an amino acid derivative. Through this strategy a chain elongation at the N-terminus has been effected. The N-deprotection and repetition of the homologation with other Se-phenyl selenocarboxylate intermediates produced b- and mixed a/b-oligopeptides without the use of coupling agents.

机译：从容易获得的和对映体富集的炔丙醇开始完成β〜3-氨基酸的立体有择合成。硒介导的碳-碳三键有机转化只能在三个步骤中完成。该方法之所以特别有吸引力，是因为反应性硒代苯基硒代羧酸酯中间体可以被氨基酸衍生物的胺官能团捕获。通过这种策略，已经实现了N末端的链延长。在不使用偶联剂的情况下，N-脱保护和与其他硒代硒代硒代羧酸硒酯中间体的同源性重复产生了b-和混合的a / b-寡肽。

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《Chemistry: A European journal》 |2009年第32期|共13页
作者
Andrea Temperini; Raffaella Terlizzi; Lorenzo Testaferri; Marcello Tiecco;
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正文语种 eng
中图分类应用化学;
关键词
oligopeptides; propargylicalcohols; selenium; amino acids;

机译：寡肽;炔丙醇;硒;氨基酸;

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1. Stereospecific Synthesis of β~3-Amino Acid Derivatives from Propargylic Alcohols: Efficient Solution-Phase Synthesis of Oligopeptides without Coupling Agents [J] . Andrea Temperini, Raffaella Terlizzi, Lorenzo Testaferri, Chemistry: A European journal . 2009,第32期

机译：从炔丙醇立体定向合成β〜3-氨基酸衍生物：无需偶联剂的寡肽高效液相合成
2. Synthesis of enantiopure trans-N-Boc-3-aminobicyclo[2.2.2]octane-2- carboxylic acids and their bicyclic 1,3-amino alcohol derivatives via the [4+2] cycloaddition of 1,3-cyclohexadiene to a chiral β-nitroacrylate [J] . Calmes M., Escale F., Didierjean C., Chirality: The pharmacological, biological, and chemical consequences of molecular asymmetry . 2011,第3期

机译：通过1,3-环己二烯的[4 + 2]环加成反应，合成对映体反式-N-Boc-3-氨基双环[2.2.2]辛烷-2-羧酸及其双环1,3-氨基醇衍生物β-硝基丙烯酸酯
3. Stereoselective Synthesis of Î²3-Amino Acids and Î²-Oligopeptides Promoted by Organoselenium Intermediates [J] . Prof. Andrea Temperinia Antonella Capperuccib Professor Alessandro DeglâInnocentib Dr. Raffaella Terlizzia amp, M Tieccoa Phosphorus, Sulfur, and Silicon and the Related Elements . 2011,第5期

机译：立体选择性合成的由有机硒中间体促进的β 3 -氨基酸和β-寡肽。
4. Highly Efficient Synthesis of Allenyltitanium Reagents Propargyl Alcohol Derivatives.Practical Synthesis of Homopargyl Alcohols [C] . Fang-Long Yang International symposium for Chinese organic chemists . 2000

机译：高效合成亚甲硝基试剂炔丙醇衍生物。常卤醇的实际合成
5. Part I. One-pot synthesis of secondary alcohols and one-pot asymmetric synthesis of secondary propargylic alcohols. Part II. Redox isomerization of secondary propargylic alcohols to enones. Part III. Synthesis study towards C9-C14 fragment of (+)-discodermolide. Part IV. Asymmetric synthesis of anti, anti-stereotriad building blocks for polypropionate natural products [D] . Xie, Qiuzhe 2007

机译：第一部分：仲醇的一锅法合成和仲炔丙醇的一锅法不对称合成。第二部分仲炔丙醇的氧化还原异构化为烯酮。第三部分（+）-discodermolide C9-C14片段的合成研究。第四部分聚丙烯酸酯天然产物的抗，抗立体三环构建基的不对称合成
6. Direct and Stereospecific Synthesis of Allenes via Reduction of Propargylic Alcohols with Cp2Zr(H)Cl [O] . Xiaotao Pu, Joseph M. Ready -1

机译：通过Cp2Zr（H）Cl还原炔丙醇直接和立体定向合成艾伦
7. Copper-catalysed cross-coupling of alkyl Grignard reagents and propargylic ammonium salts: stereospecific synthesis of allenes [O] . Manuel Guisán-Ceinos, Victor Martín-Heras, Rita Soler-Yanes, 2018

机译：烷基格子试剂和丙基铵盐的铜催化的交叉偶联：立体特异性合成烯丙烯

Stereospecific Synthesis of β~3-Amino Acid Derivatives from Propargylic Alcohols: Efficient Solution-Phase Synthesis of Oligopeptides without Coupling Agents

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