(2R)-2,3-dihydro-N-(S)-α-methylbenzyl-2-phenyl-4-pyridone

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (2R)-2,3-dihydro-N-(S)-α-methylbenzyl-2-phenyl-4-pyridone
• 英文别名: (2R)-2-phenyl-1-[(1S)-1-phenylethyl]-2,3-dihydropyridin-4-one
• 化学式: C₁₉H₁₉NO
• 分子量: 277.366
• InChiKey: YHSZAJTZWUPHRK-HNAYVOBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (S)-(-)- α-甲基苄胺 在 (R)-binaphthol 、 4 A molecular sieve 、 三苯基硼酸酯 、 magnesium sulfate 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 12.0h， 生成 (2R)-2,3-dihydro-N-(S)-α-methylbenzyl-2-phenyl-4-pyridone
  参考文献：
  名称：

  A New Chiral BLA Promoter for Asymmetric Aza Diels-Alder and Aldol-Type Reactions of Imines

  摘要：

  A new type of chiral promoter for double asymmetric inductions of aza Diels-Alder and aldol-type reactions of imines is prepared from trialkyl berates (B(OMe)(3) or B(OPh)(3)) and optically pure binaphthol; X-ray analysis of the boron complex demonstrates that it exists as a Bronsted acid-assisted chiral Lewis acid(BLA). The aldol-type reactions of a number of N-benzhydrylimines derived from aromatic aldehydes with the ketene silyl acetal derived from tert-butyl acetate mediated by the chiral BLA afford beta-amino acid esters with high enantioselectivity. The solution conformations of the BLA.imine complexes have been studied using H-1 NMR analysis and difference NOE measurements. The absolute configurations of the adducts can be understood in terms of a rational model involving an intramolecular hydrogen binding interaction via a Bronsted acid.

  DOI：

  10.1021/ja00102a019

文献信息

• Asymmetric aza-Diels-Alder reaction: enantio- and diastereoselective reaction of imine mediated by Chiral Lewis acid
  作者：Kouji Hattori、Hisashi Yamamoto

  DOI：10.1016/s0040-4020(01)80532-9

  日期：1993.2

  asymmetric aza-Diels-Alder reaction using chiral boron mediator is developed. The key to its success is the use of the chiral boron complex prepared in situ from (R)- or (S)- binaphthol and B(OPh)3. The enantiomeric reaction of prochiral imine affords products of up to 90% ee. The double asymmetric induction of chiral imine using α-benzylamine as a chiral auxiliary is achieved with almost complete diastereoselectivity

  开发了一种有效的使用手性硼介体的不对称aza-Diels-Alder反应。其成功的关键是使用由（R）-或（S）-联萘酚和B（OPh）3原位制备的手性硼配合物。前手性亚胺的对映体反应可提供高达90％ee的产物。使用α-苄基胺作为手性助剂，可以实现对脂肪族和芳香族亚胺几乎完全非对映选择性的手性亚胺的双不对称诱导。该方法适用于高效合成哌啶生物碱的鸟嘌呤和芥氨酸。
• Aza Diels–Alder reactions utilizing 4-iodo-2-trimethylsilyloxy-butadiene
  作者：Cody Timmons、Adiseshu Kattuboina、Lauren McPherson、James Mills、Guigen Li

  DOI：10.1016/j.tet.2005.10.018

  日期：2005.12

  The aza Diels-Alder reaction is described for a novel diene. Imines bearing benzyl and aromatic protecting groups both work well. Moderate diastereoselectivities can be obtained using the simple alpha-methylbenzyl chiral auxiliary. (c) 2005 Elsevier Ltd. All rights reserved.
• A New Chiral BLA Promoter for Asymmetric Aza Diels-Alder and Aldol-Type Reactions of Imines
  作者：Kazuaki Ishihara、Mayumi Miyata、Kouji Hattori、Toshiji Tada、Hisashi Yamamoto

  DOI：10.1021/ja00102a019

  日期：1994.11

  A new type of chiral promoter for double asymmetric inductions of aza Diels-Alder and aldol-type reactions of imines is prepared from trialkyl berates (B(OMe)(3) or B(OPh)(3)) and optically pure binaphthol; X-ray analysis of the boron complex demonstrates that it exists as a Bronsted acid-assisted chiral Lewis acid(BLA). The aldol-type reactions of a number of N-benzhydrylimines derived from aromatic aldehydes with the ketene silyl acetal derived from tert-butyl acetate mediated by the chiral BLA afford beta-amino acid esters with high enantioselectivity. The solution conformations of the BLA.imine complexes have been studied using H-1 NMR analysis and difference NOE measurements. The absolute configurations of the adducts can be understood in terms of a rational model involving an intramolecular hydrogen binding interaction via a Bronsted acid.