(1S,2S)-1-(2-furyl)-2-nitropropylcarbamic acid tert-butyl ester

• 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: (1S,2S)-1-(2-furyl)-2-nitropropylcarbamic acid tert-butyl ester
• 英文别名: tert-butyl (1R,2S)-2-nitro-1-(2-furyl)propylcarbamate；tert-butyl (1R,2S)-(1-(furan-2-yl)-2-nitropropyl)carbamate；(1R,2S)-tert-butyl 1-(furan-2-yl)-2-nitropropylcarbamate；tert-butyl N-[(1R,2S)-1-(furan-2-yl)-2-nitropropyl]carbamate
• 化学式: C₁₂H₁₈N₂O₅
• 分子量: 270.285
• InChiKey: RLBIKFMQRRNBQG-WCBMZHEXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  97.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  硝基乙烷 、 (E)-tert-butyl furan-2-ylmethylenecarbamate 在 chiral Cu-catalyst 4-叔丁基苯酚 、 samarium(III) isopropoxide 作用下， 以 四氢呋喃 为溶剂， 反应 49.0h， 生成 (1S,2S)-1-(2-furyl)-2-nitropropylcarbamic acid tert-butyl ester 、 (1R,2R)-1-(2-furyl)-2-nitropropylcarbamic acid tert-butyl ester
  参考文献：
  名称：

  syn-Selective Catalytic Asymmetric Nitro-Mannich Reactions Using a Heterobimetallic Cu−Sm−Schiff Base Complex

  摘要：

  syn-Selective catalytic asymmetric nitro-Mannich reactions using a heterobimetallic Cu/Sm/Schiff base complex are described. The present method is complementary to the previously reported methods, and products were obtained in high syn-selectivity (> 20:1), yield (99-62%), and enantioselectivity (98-83% ee). Both Cu and Sm metals, aligned suitably in a dinucleating Schiff base ligand, were essential to realize high synselectivity.

  DOI：

  10.1021/ja0701560

文献信息

• Highly Enantioselective Nitro-Mannich Reaction Catalyzed by <i>Cinchona</i> Alkaloids and <i>N</i>-Benzotriazole Derived Ammonium Salts
  作者：Yu Wei、Wei He、Yulong Liu、Peng Liu、Shengyong Zhang

  DOI：10.1021/ol203170x

  日期：2012.2.3

  catalytic enantio- and diastereoselective nitro-Mannich reaction of α-amido sulfones in the mixed solvent of toluene/H2O has been realized using a phase-transfer catalyst (PTC) derived from cinchona alkaloids and N-benzotriazole. It performed well over a wide range of substrates to give the desired products in good yields (up to 94%) with excellent enantioselectivities (up to 99% ee) and diastereoselectivities

  使用衍生自金鸡纳生物碱和N-苯并三唑的相转移催化剂（PTC）实现了α-酰胺基砜在甲苯/ H 2 O混合溶剂中的催化对映体和非对映体的硝基曼尼希反应。它在各种底物上均表现良好，以高收率（最高94％）提供所需的产品，并具有出色的对映选择性（最高99％ee）和非对映选择性（最高99：1）。
• Dinuclear Zinc-Catalyzed Enantioselective Aza-Henry Reaction
  作者：Barry M. Trost、David W. Lupton

  DOI：10.1021/ol070618e

  日期：2007.5.1

  The dinuclear zinc catalyst 1a was found to catalyze the addition of nitroalkanes to carbamate-protected imines. This aza-Henry reaction proceeds with high enantioselectivity when various carbamate-protected imines are used. alpha,beta-Unsaturated imines proved to be a particularly useful class of substrate routinely giving the alpha-nitro amine products in high enantiomeric excess.

  发现双核锌催化剂1a催化将硝基烷烃加到氨基甲酸酯保护的亚胺上。当使用各种氨基甲酸酯保护的亚胺时，该氮杂-亨利反应以高对映选择性进行。事实证明，α，β-不饱和亚胺是一类特别有用的底物，通常以高对映体过量的形式产生α-硝基胺产物。
• Doubly Stereocontrolled Asymmetric Aza-Henry Reaction with<i>in situ</i>Generation of<i>N</i>-Boc-Imines Catalyzed by Novel Rosin-Derived Amine Thiourea Catalysts
  作者：Xianxing Jiang、Yifu Zhang、Lipeng Wu、Gen Zhang、Xing Liu、Hailong Zhang、Dan Fu、Rui Wang

  DOI：10.1002/adsc.200900413

  日期：2009.9

  doubly stereocontrolled organocatalytic aza-Henry reaction of nitroalkanes to N-Boc-imines generated in situ from a variety of substituted α-amido sulfones was investigated for the first time, in general, affording the corresponding products with high to excellent yields (up to 93% yield) and enantioselectivities (up to 98% ee), and satisfactory diastereoselectivies (anti/syn up to 98:2). Furthermore

  首次研究了硝基烷烃与由多种取代的α-酰胺基砜原位生成的N -Boc-亚胺的双重立体控制的有机催化氮杂-亨利反应，通常可提供具有高到极好的收率的相应产品（最高93％的收率）和对映体选择性（高达98％ee）和令人满意的非对映体选择性（抗/ syn高达98：2）。此外，已经证明这些基于松香的有机催化剂与金鸡纳生物碱衍生的催化剂一起是该催化不对称过程的非常有效的促进剂。
• Asymmetric aza-Henry reaction of BOC-protected imines with zinc-FAM catalyst
  作者：Nurzhan Beksultanova、Özdemir Doğan

  DOI：10.1080/00397911.2024.2303054

  日期：2024.3.3

  Derivatives of ferrocenyl-substituted aziridinyl methanol (FAM) ligands were used with zinc metal for asymmetric aza-Henry (nitro-aldol) reaction of N-Boc protected imines with nitroalkanes. At opt...

  二茂铁基取代的氮丙啶基甲醇 (FAM) 配体的衍生物与锌金属一起用于 N-Boc 保护的亚胺与硝基烷烃的不对称氮杂亨利（硝基醇醛）反应。在选择...
• Highly Enantioselective Thiourea-Catalyzed Nitro-Mannich Reactions
  作者：Tehshik P. Yoon、Eric N. Jacobsen

  DOI：10.1002/anie.200461814

  日期：2005.1.7