tert-butyl (2R,4R)-2-formyl-4-hydroxypyrrolidine-1-carboxylate | 1346163-10-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: tert-butyl (2R,4R)-2-formyl-4-hydroxypyrrolidine-1-carboxylate
• 英文别名: (4R)-N-Boc-4-hydroxy-(2R)-prolinal
• CAS: 1346163-10-7
• 化学式: C₁₀H₁₇NO₄
• 分子量: 215.249
• InChiKey: YPLPEMVHSNXIKV-HTQZYQBOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl (2R,4R)-2-formyl-4-hydroxypyrrolidine-1-carboxylate 在 三乙烯二胺 、 盐酸 作用下， 以 水 、 甲苯 为溶剂， 反应 96.5h， 生成 (1S,6R,7aR)-1,6-dihydroxy-2-methylenetetrahydro-1H-pyrrolizin-3(2H)-one
  参考文献：
  名称：

  An asymmetric substrate-controlled Morita–Baylis–Hillman reaction as approach for the synthesis of pyrrolizidinones and pyrrolizidines

  摘要：

  We describe herein an approach to the total synthesis of functionalized pyrrolizidinones and pyrrolizidines. The synthetic sequence is based on a highly stereoselective substrate-controlled Morita-Baylis-Hillman (MBH) reaction between a chiral amino-aldehyde and methyl acrylate. The selectivity attained in this reaction was controlled by the presence of a hydroxyl group adequately placed in the structure of the amino-aldehyde used as the nucleophilic component of the MBH reaction. The MBH adducts were used as substrate for an efficient total synthesis of pyrrolizidinones and pyrrolizidines in good overall yield. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.10.050
• 作为产物：
  描述：

  N-α-tert-butyloxycarbonyl-cis-4-hydroxy-D-proline ethyl ester 在 二异丁基氢化铝 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 0.33h， 以91%的产率得到tert-butyl (2R,4R)-2-formyl-4-hydroxypyrrolidine-1-carboxylate
  参考文献：
  名称：

  An asymmetric substrate-controlled Morita–Baylis–Hillman reaction as approach for the synthesis of pyrrolizidinones and pyrrolizidines

  摘要：

  We describe herein an approach to the total synthesis of functionalized pyrrolizidinones and pyrrolizidines. The synthetic sequence is based on a highly stereoselective substrate-controlled Morita-Baylis-Hillman (MBH) reaction between a chiral amino-aldehyde and methyl acrylate. The selectivity attained in this reaction was controlled by the presence of a hydroxyl group adequately placed in the structure of the amino-aldehyde used as the nucleophilic component of the MBH reaction. The MBH adducts were used as substrate for an efficient total synthesis of pyrrolizidinones and pyrrolizidines in good overall yield. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.10.050

文献信息

• Heck Reaction on Morita-Baylis-Hillman Adducts: Diastereoselective Synthesis of Pyrrolizidinones and Pyrrolizidines
  作者：Fernando Coelho、Kristerson de Luna Freire、Cláudio Tormena

  DOI：10.1055/s-0030-1261161

  日期：2011.9

  An efficient approach to the diastereoselective synthesis of benzylidene-, benzyl-pyrrolizidinones, and pyrrolizidines is described. The sequence is based on a highly stereoselective Heck ­reaction between a hydroxylated pyrrolizidinone, prepared from a Morita-Baylis-Hillman adduct, and a suitable aryl halide, using Nájera’s oxime derived palladacycle as catalyst.

  本文介绍了一种非对映选择性合成亚苄基、苄基吡咯烷酮和吡咯烷类化合物的有效方法。该步骤基于由 Morita-Baylis-Hillman 加合物制备的羟基吡咯烷酮与合适的芳基卤化物之间的高立体选择性 Heck 反应，并使用 Nájera 的肟衍生帕拉代环作为催化剂。