threo-N-(3-hydroxy-2-methyl-3-phenylpropanoyl)pyrrolidine

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: threo-N-(3-hydroxy-2-methyl-3-phenylpropanoyl)pyrrolidine
• 英文别名: (2SR,3RS)-N-(3-hydroxy-2-methyl-3-phenylpropionyl)pyrrolidine；(2R,3S)-3-hydroxy-2-methyl-3-phenyl-1-pyrrolidin-1-ylpropan-1-one
• 化学式: C₁₄H₁₉NO₂
• 分子量: 233.31
• InChiKey: BJTISXFLIHVHBI-YPMHNXCESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (2RS, 3SR)-3-hydroxy-2-methyl-3-phenylpropanoic acid 在 吡啶 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 threo-N-(3-hydroxy-2-methyl-3-phenylpropanoyl)pyrrolidine
  参考文献：
  名称：

  Rational Design of an l-Histidine-Derived Minimal Artificial Acylase for the Kinetic Resolution of Racemic Alcohols

  摘要：

  This communication describes the rational design of an l-histidine-derived minimal artificial acylase. Our new artificial acylase, tert-butyldiphenylsilyl ether of N-(2,4,6-triisopropylbenzenesulfonyl)-pi(Me)-l-histidinol, is a simple and small molecule (molecular weight = 660) that contains only one chiral carbon center that originates from natural l-histidine. The kinetic acylation of racemic secondary alcohols induced by this compound showed an S (kfast/kslow) value of up to 93. A reusable polystyrene-bound artificial acylase was also developed to examine its practical usability.

  DOI：

  10.1021/ja045850j

文献信息

• Enantioselective Aldol and Michael Additions of Achiral Enolates in the Presence of Chiral Lithium Amides and Amines
  作者：Eusebio Juaristi、Albert K. Beck、Jesper Hansen、Thomas Matt、Triptikumar Mukhopadhyay、Malgorzata Simson、Dieter Seebach

  DOI：10.1055/s-1993-26041

  日期：——

  It is now well established that lithium enolates and analogous derivatives generally exist as complex structures held together by noncovalent bonds ("supramolecules"). In particular, Li enolates aggregate to give dimers, tetramers, and higher oligomers, whose metal centers may be complexed by solvent molecules or chelating ligands. In addition, the anionoid part of the enolates may hydrogen-bond to weak acids such as secondary amines. Furthermore, such supramolecules can be product-forming species in synthetic reactions of Li enolates. This paper describes our observations of the temporary incorporation of chiral amines or chiral lithium amides into achiral lithium enolate aggregates (an interaction which is simply broken during aqueous workup!) to give enantiomerically enriched products. In particular, enantioselective aldol and Michael additions between achiral enolates and achiral aldehydes or achiral nitroolefins have been achieved in the presence of several chiral amines (or their lithium amides) derived from (S)-valine or (R,R)-tartaric acid. Finally, this report demonstrates the potential usefulness in asymmetric synthesis of ortho lithiation directed by chiral α-aminoalkoxides.

  目前已经充分确定，锂烯醇盐及其类似衍生物通常以非共价键结合而成的复杂结构（“超分子”）存在。特别是，锂烯醇盐聚集形成二聚体、四聚体和高阶寡聚体，其金属中心可能被溶剂分子或螯合配体络合。此外，烯醇盐的阴离子部分可能与二级胺等弱酸形成氢键。而且，这些超分子在锂烯醇盐的合成反应中可能是产物形成物种。本文描述了我们观察到的将手性胺或手性锂酰胺暂时掺入非手性锂烯醇盐聚集体（在水中处理时这种相互作用被简单破坏！）从而产生手性富集产物的现象。特别是，在几种由(S)-缬氨酸或(R,R)-酒石酸衍生的手性胺（或它们的锂酰胺）存在下，实现了非手性烯醇盐与非手性的醛或非手性硝基烯烃的立体选择性羟醛缩合反应和迈克尔加成反应。最后，本报告展示了手性α-氨基烷氧基导向的邻位锂化在对映选择性合成中的潜在应用价值。
• Aldol diastereoselection zirconium enolates. Product-selective, enolate structure independent condensations.
  作者：D.A. Evans、L.R. McGee

  DOI：10.1016/s0040-4039(00)92848-x

  日期：1980.1

  Both(E)- and (Z)-zirconium enolates have been shown to undergo selective kinetic aldol condensation to give mainly erythro-β-hydroxy ketones, esters and amides.

  已证明（E）-和（Z）-锆烯醇盐都经历选择性的动力学羟醛缩合，主要得到赤型-β-羟基酮，酯和酰胺。
• Stereoselective aldol reactions via titanium enolates
  作者：Patrick J. Murphy、Garry Procter、Andrew T. Russell

  DOI：10.1016/s0040-4039(00)96039-8

  日期：1987.1

  The species produced by treatment of the lithium enolate of N-propionylpyrroldine with bis(cyclopentadienyl)titanium dichloride adds to simple aldehydes with high stereoselectivity to give anti-aldol products.

  通过用双（环戊二烯基）钛二氯化物处理N-丙酰基吡咯烷锂的烯醇锂产生的物质增加了具有高立体选择性的简单醛，从而得到了抗醛醇缩合产物。
• Fluoride ion-catalyzed reduction of aldehydes and ketones with hydrosilanes. Synthetic and mechanistic aspects and an application to the threo-directed reduction of .alpha.-substituted alkanones
  作者：Makoto Fujita、Tamejiro Hiyama

  DOI：10.1021/jo00258a003

  日期：1988.11
• Highly stereoselective reduction of .alpha.-substituted .beta.-keto amides by means of hydrosilane-fluoride ion and hydrosilane-acid reagent. A practical approach to aldols of both threo and erythro configurations
  作者：Makoto Fujita、Tamejiro Hiyama

  DOI：10.1021/ja00312a098

  日期：1985.12