(2S,3R) ethyl 3-hydroxy-2-ethylbenzenepropanoate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: (2S,3R) ethyl 3-hydroxy-2-ethylbenzenepropanoate
• 英文别名: (2S,3R)-2-ethyl-3-hydroxy-3-phenylpropionic acid ethyl ester；(S)-ethyl 2-((R)-hydroxy(phenyl)methyl)butanoate；ethyl (2S)-2-[(R)-hydroxy(phenyl)methyl]butanoate
• 化学式: C₁₃H₁₈O₃
• 分子量: 222.284
• InChiKey: MCJORAPHPVJYNZ-RYUDHWBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-乙氧甲酰苯丁酮 在 (R,R)-cobalt(II) 、 sodium methylate 四氢糠醇 、 sodium tetrahydroborate 、 乙醇 作用下， 以 氯仿 为溶剂， 反应 15.0h， 以88%的产率得到(2S,3R) ethyl 3-hydroxy-2-ethylbenzenepropanoate
  参考文献：
  名称：

  旋光性钴配合物催化对映选择性硼氢化物的还原。

  摘要：

  在催化量的光学活性钴（II）络合物催化剂的存在下，芳香族酮或亚胺对映体的高度对映选择性硼氢化物还原。该对映选择性还原是使用精确预改性的硼氢化物与醇（例如四氢糠醇，乙醇和甲醇）进行的。通过选择合适的醇作为改性剂和合适的催化剂β-酮亚氨基配体，可以获得高的光学收率。对映选择性硼氢化物还原已成功应用于光学活性的1,3-二醇的制备，双酰基二茂铁的立体选择性还原以及1,3-二羰基化合物的动态和/或动力学拆分。

  DOI：

  10.1002/chem.200304794

文献信息

• Lewis Base Activation of Lewis Acids:  Catalytic, Enantioselective Addition of Silyl Ketene Acetals to Aldehydes
  作者：Scott E. Denmark、Gregory L. Beutner、Thomas Wynn、Martin D. Eastgate

  DOI：10.1021/ja047339w

  日期：2005.3.1

  The concept of Lewis base activation of Lewis acids has been reduced to practice for catalysis of the aldol reaction of silyl ketene acetals and silyl dienol ethers with aldehydes. The weakly acidic species, silicon tetrachloride (SiCl4), can be activated by binding of a strongly Lewis basic chiral phosphoramide, leading to in situ formation of a chiral Lewis acid. This species has proven to be a competent

  路易斯酸的路易斯碱活化的概念已被简化用于催化甲硅烷基乙烯酮缩醛和甲硅烷基二烯醇醚与醛的羟醛反应。弱酸性物质四氯化硅 (SiCl4) 可以通过结合强路易斯碱性手性磷酰胺而被激活，导致手性路易斯酸的原位形成。该物质已被证明是将乙酸酯、丙酸酯和异丁酸酯衍生的甲硅烷基乙烯酮缩醛与共轭和非共轭醛进行羟醛加成反应的有效催化剂。此外，还证明了甲硅烷基二烯醇醚的乙烯基羟醛反应。高水平的区域-，抗非对映-，
• Dynamic Kinetic Resolution with Enantioselective Borohydride Reduction Catalyzed by Optically Active β-Ketoiminato Cobalt(II) Complexes: Highly Diastereo- and Enantioselective Preparation of Optically Active<i>anti</i>-Aldol Compounds
  作者：Yuhki Ohtsuka、Daichi Miyazaki、Taketo Ikeno、Tohru Yamada

  DOI：10.1246/cl.2002.24

  日期：2002.1

  Optically active anti-2-alkyl-3-hydroxy esters were stereoselectively obtained from the corresponding 2-alkyl-3-keto esters using enantioselective borohydride reduction along with dynamic kinetic resolution in the presence of optically active β-ketoiminato cobalt complex catalysts. The reduction system provided an alternative preparation for anti-aldol compounds with high diastereo- and enantioselectivities

  在光学活性β-酮亚氨基钴配合物催化剂存在下，使用对映选择性硼氢化物还原以及动态动力学拆分，从相应的2-烷基-3-酮酯立体选择性地获得了光学活性的抗2-烷基-3-羟基酯。该还原系统为具有高非对映选择性和对映选择性的抗羟醛化合物提供了另一种制备方法。
• A NEW METHOD FOR THE SYNTHESIS OF β-HYDROXYESTERS BY USING METALLIC TIN
  作者：Taira Harada、Teruaki Mukaiyama

  DOI：10.1246/cl.1982.161

  日期：1982.2.5

  Metallic tin or activated metallic tin, prepared by reduction of stannous chloride with lithium aluminum hydride, smoothly reacts with α-haloesters to yield tin enolates, which in turn react with carbonyl compounds under mild conditions to give, after hydrolysis, β-hydroxyesters in high yields.

  用氢化铝锂还原氯化亚锡制备的金属锡或活化金属锡，与α-卤代酯平稳反应生成烯醇锡，然后在温和条件下与羰基化合物反应，水解后生成β-羟基酯。产量。
• Surface-Mediated Solid Phase Reaction. IX. A Convenient Procedure for Aldol Reaction of Ketene Silyl Acetals with Aldehydes on the Solid Surface of Alumina
  作者：Brindaban C. Ranu、Manika Saha、Sanjay Bhar

  DOI：10.1080/00397919708005012

  日期：1997.9

  The aldol reaction of ketene silyl acetals with aldehydes proceeds efficiently on the solid surface of alumina impregnated with anhydrous zinc chloride under sonication providing aldol products in high yields and with good stereoselectivity.
• Enolboration. 6. Dicyclohexyliodoborane, a Versatile Reagent for the Stereoselective Synthesis of Either Z or E Enolates from Representative Esters
  作者：Kumaraperumal Ganesan、Herbert C. Brown

  DOI：10.1021/jo00088a012

  日期：1994.5

  A smooth, rapid, quantitative, and highly stereoselective synthesis of either Z or E enolates from representative esters has been achieved with dicyclohexyliodoborane, Chx(2)BI, in the presence of a suitable tertiary amine, such as triethylamine or N,N-diisopropylethylamine. A systematic investigation of the enolboration of ethyl propionate and ethyl phenylacetate, as model esters, by the various Chx(2)BX and BX-9-BBN reagents (X = OMs, I, and Br) established Chx(2)BI as the preferred reagent in terms of yield and selectivity. Further study of representative esters (RCH(2)-COOR') with Chx(2)BI established that the steric requirements of both the alkyl group (R) at the ct-position and the alkoxy group (OR') play a significant role in controlling the enolate geometry. The steric requirements of the amine (R''N-3) also contribute considerably to the stereoselectivity of the reaction, The present study provides a simple procedure for the synthesis of Z or E enol borinates from representative esters (RCH(2)COOR') using the combined stereodirecting effects of the alkyl (R) and the alkoxy (OR') groups. These enol borinates are highly reactive with aldehydes at temperatures as low as -78 degrees C and are exceptionally stereoselective even at 0 degrees C, In this exploratory study, the synthesis of stereoselective enolates from representative esters (RCH(2)COOR') using Chx(2)BI/R''N-3 is discussed, with special emphasis on the effects of the steric requirements of R and OR' in controlling the enolate geometry.