(2R,3R)-2-methylethyl-4-nitro-3-(thiophen-2-yl)butanal

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: (2R,3R)-2-methylethyl-4-nitro-3-(thiophen-2-yl)butanal
• 英文别名: (2R,3R)-2-isopropyl-4-nitro-3-(thiophen-2-yl)butanal；2-isopropyl-4-nitro-3-thiophen-2-yl butyraldehyde；(2R,3R)-4-nitro-2-propan-2-yl-3-thiophen-2-ylbutanal
• 化学式: C₁₁H₁₅NO₃S
• 分子量: 241.311
• InChiKey: UYXBCASIEJKCFC-VHSXEESVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  91.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-硝基乙烯基噻吩 、 异戊醛 在 (2S)-N-tritylpyrrolidine-2-carboxamide 、 苯甲酸 作用下， 以 甲苯 为溶剂， 反应 24.5h， 以89%的产率得到(2R,3R)-2-methylethyl-4-nitro-3-(thiophen-2-yl)butanal
  参考文献：
  名称：

  Aromatic l-prolinamide-catalyzed asymmetric Michael addition of aldehydes to nitroalkenes

  摘要：

  Two chiral aromatic L-prolinamides were synthesized in high overall yield (95%) from N-Boc-L-proline and served as organocatalysts in asymmetric Michael reactions of aldehydes to nitroalkenes. Under the optimized reaction conditions, (S)-N-tritylpyrrolidine-2-carboxamide 4 was found to be a highly efficient organocatalyst for the Michael addition, and the corresponding Michael adducts were obtained in good yields (up to 94%), with excellent enantioselectivities (up to 99% ee) and diastereoselectivities (up to 99:1 dr). (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2014.11.006

文献信息

• Novel Prolinamide–Camphor-Containing Organocatalysts for Direct Asymmetric Michael Addition of Unmodified Aldehydes to Nitroalkenes
  作者：Raju Jannapu Reddy、Hsuan-Hao Kuan、Tsai-Yung Chou、Kwunmin Chen

  DOI：10.1002/chem.200901254

  日期：2009.9.21

  The asymmetric challenge! New camphor‐based prolinamides were designed, synthesized, and proven to be a highly efficient organocatalysts for asymmetric Michael reactions. Treatment of unmodified aldehydes with nitroalkenes in the presence of 5–10 mol % organocatalysts provided the desired Michael products in high chemical yields (up to 94 %) and high to excellent levels of diastereo‐ and enantioselectivities

  不对称的挑战！设计，合成并基于樟脑的新脯氨酰胺是一种用于不对称迈克尔反应的高效有机催化剂。在5-10 mol％的有机催化剂存在下用硝基烯烃处理未改性的醛，可提供所需的迈克尔产品，化学收率高（高达94％），非对映和对映选择性高（至99：1 dr和>）。 99％  ee）。
• Enantioselective Michael addition of aldehydes to nitroolefins catalyzed by pyrrolidine-HOBt
  作者：Togapur Pavan Kumar、Mohammad Abdul Sattar、Sthanikam Siva Prasad、Kothapalli Haribabu、Cirandur Suresh Reddy

  DOI：10.1016/j.tetasy.2017.02.005

  日期：2017.3

  The oxytriazole catalyst "pyrrolidine-HOBt" developed for asymmetric Michael addition of cyclohexanone to nitroolefins is now evaluated for the asymmetric Michael addition of aldehydes to nitroolefins under similar reaction conditions. The results of this study indicate that, the oxytriazole catalyst "pyrrolidine-HOBt" is equally effective in promoting the Michael addition of aldehydes to nitroolefins on employing benzoic acid as an additive. The desired products, gamma-nitrocarbonyl compounds were obtained in good yields and high enantioselectivities. (C) 2017 Elsevier Ltd. All rights reserved.
• Betancort, Juan M.; Sakthivel, Kandasamy; Thayumanavan, Rajeswari, Synthesis, 2004, # 9, p. 1509 - 1521
  作者：Betancort, Juan M.、Sakthivel, Kandasamy、Thayumanavan, Rajeswari、Tanaka, Fujie、Barbas III, Carlos F.

  DOI：——

  日期：——
• Catalytic Direct Asymmetric Michael Reactions:  Taming Naked Aldehyde Donors
  作者：Juan M. Betancort、Carlos F. Barbas

  DOI：10.1021/ol0167006

  日期：2001.11.1

  [GRAPHICS]Direct catalytic enantio- and diastereoselective Michael addition reactions of unmodified aldehydes to nitro olefins using (S)-2-(morpholinomethyl)-pyrrolidine as a catalyst are described. The reactions proceed in good yield (up to 96%) in a highly syn-selective manner (up to 98:2) with enantloselectivities approaching 80%. The resulting gamma -formyl nitro compounds are readily converted to chiral, nonracemic 3,4-disubstituted pyrrolidines.
• Asymmetric Michael addition of aldehydes to nitroolefins catalyzed by a pyrrolidine–pyrazole
  作者：Togapur Pavan Kumar

  DOI：10.1016/j.tetasy.2014.07.005

  日期：2014.10

  An effective protocol for the stereoselective Michael addition of aldehydes to nitroolefins using pyrrolidine-pyrazole as an organocatalyst is described. The catalytic cycle was found to be productive in terms of yield and selectivity, when performed under solvent-free reaction conditions and employing 15 mol % of catalyst and 10 mol % of benzoic acid at room temperature. (C) 2014 Elsevier Ltd. All rights reserved.