dimethyl (2R,3R,4R,5S)-3-(dimethoxymethyl)-1-(4-methylphenyl)sulfonyl-5-phenylpyrrolidine-2,4-dicarboxylate | 130159-77-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: dimethyl (2R,3R,4R,5S)-3-(dimethoxymethyl)-1-(4-methylphenyl)sulfonyl-5-phenylpyrrolidine-2,4-dicarboxylate
• CAS: 130159-77-2
• 化学式: C₂₄H₂₉NO₈S
• 分子量: 491.562
• InChiKey: SPGNGWNHXGCMCH-XRXFAXGQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  117
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  2-O-tert-butyl 4-O-methyl (2R,3R,4R,5S)-3-[(4R,5R)-1,3-dimethyl-4,5-diphenylimidazolidin-2-yl]-5-phenylpyrrolidine-2,4-dicarboxylate 在 硫酸 、 三乙胺 作用下， 以 氯仿 为溶剂， 反应 27.0h， 生成 dimethyl (2R,3R,4R,5S)-3-(dimethoxymethyl)-1-(4-methylphenyl)sulfonyl-5-phenylpyrrolidine-2,4-dicarboxylate
  参考文献：
  名称：

  Diastereoselective cycloaddition of N-lithiated azomethine ylides to (E)-.alpha.,.beta.-unsaturated esters bearing a C2-symmetric imidazolidine chiral controller

  摘要：

  The 1,3-dipolar cycloaddition of N-metalated azomethine ylides to chiral (E)-3-(1,3-disubstituted 4,5-diphenylimidazolidin-2-yl)propenoates proceeded highly diastereoselectively. The previously unknown absolute configuration of optically pure 1,2-dianilino-1,2-diphenylethane was determined from the absolute configuration of the cycloadducts. What diastereotopic olefin face of the alpha,beta-unsaturated ester was attacked by the ylide was found to depend dramatically upon the nature of N substituents of the chiral controller as well as upon the bulkiness of the ester moiety of the ylide.

  DOI：

  10.1021/jo00014a028

文献信息

• Asymmetric Cycloaddition of<i>N</i>-Metalated Azomethine Ylides with the Optically Active α,β-Unsaturated Esters Derived from α-Amino Acids
  作者：Shuji Kanemasa、Hidetoshi Yamamoto、Eiji Wada、Tosio Sakurai、Kunio Urushido

  DOI：10.1246/bcsj.63.2857

  日期：1990.10

  α,β-Unsaturated esters bearing a chiral oxazolidine or perhydropyrrolo[1,2-c]imidazole auxiliary at the β-position have been prepared and applied to the cycloadditions with N-metalated azomethine ylides derived from α-(benzylideneamino) esters. These reactions are found to proceed with an exclusively high diastereofacial selectivity to give 2,4-pyrrolidinedicarboxylates with four consecutive chiral

  已经制备了在 β 位带有手性恶唑烷或全氢吡咯并 [1,2-c] 咪唑助剂的 α,β-不饱和酯，并将其应用于与衍生自 α-（亚苄基氨基）酯的 N-金属化偶氮甲碱叶立德的环加成反应。发现这些反应以独特的高非对映选择性进行，在去除手性助剂后得到具有四个连续手性中心的 2,4-吡咯烷二羧酸盐。讨论了过渡态的详细立体化学。
• Asymmetric 1,3-dipolar cycloadditions of azomethine ylides with a chiral electron-deficient olefinic dipolarophile
  作者：Kanemasa Shuji、Yamamoto Hidetoshi

  DOI：10.1016/s0040-4039(00)94463-0

  日期：1990.1

  The first example of efficient asymmetric 1,3-dipolar cycloadditions of azomethine ylides is presented, where reactive N-metalated azomethine ylides and the α,β-unsaturated ester with a chiral perhydropyrrolo[1,2—c]imidazol-3-yl moiety at the β-position have been employed. The exclusive participation of thermodynamically less stable 3-H/3′-H synperiplanar conformer is based on its sterical preference

  给出了高效有效的不对称1,3-偶极偶氮甲亚胺环加成反应的第一个例子，其中反应性N-金属化的偶氮甲亚胺和具有手性过氢吡咯并[1,2 - c ]咪唑-3-基的α，β-不饱和酯在β-位已被采用。热力学不稳定的3-H / 3'-H上平面共形异构体的排他性参与是基于其在边界轨道和螯合控制的刚性游离态中的空间偏好。
• KANEMASA, SHUJI;YAMAMOTO, HIDETOSHI, TETRAHEDRON LETT., 31,(1990) N5, C. 3633-3636
  作者：KANEMASA, SHUJI、YAMAMOTO, HIDETOSHI

  DOI：——

  日期：——
• KANEMASA, SHUJI;YAMAMOTO, HIDETOSHI;WADA, EIJI;SAKURAI, TOSIO;URUSHIDO, K+, BULL. CHEM. SOC. JAP., 63,(1990) N0, C. 2857-2865
  作者：KANEMASA, SHUJI、YAMAMOTO, HIDETOSHI、WADA, EIJI、SAKURAI, TOSIO、URUSHIDO, K+

  DOI：——

  日期：——
• Diastereoselective cycloaddition of N-lithiated azomethine ylides to (E)-.alpha.,.beta.-unsaturated esters bearing a C2-symmetric imidazolidine chiral controller
  作者：Shuji Kanemasa、Takeshi Hayashi、Junji Tanaka、Hidetoshi Yamamoto、Tosio Sakurai

  DOI：10.1021/jo00014a028

  日期：1991.7

  The 1,3-dipolar cycloaddition of N-metalated azomethine ylides to chiral (E)-3-(1,3-disubstituted 4,5-diphenylimidazolidin-2-yl)propenoates proceeded highly diastereoselectively. The previously unknown absolute configuration of optically pure 1,2-dianilino-1,2-diphenylethane was determined from the absolute configuration of the cycloadducts. What diastereotopic olefin face of the alpha,beta-unsaturated ester was attacked by the ylide was found to depend dramatically upon the nature of N substituents of the chiral controller as well as upon the bulkiness of the ester moiety of the ylide.