(4S,5R)-3-(tert-Butoxycarbonyl)-2,2-dimethyl-5-isopropyl-4-(N-methoxy-N-methylcarbamoyl)oxazolidine | 163625-43-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (4S,5R)-3-(tert-Butoxycarbonyl)-2,2-dimethyl-5-isopropyl-4-(N-methoxy-N-methylcarbamoyl)oxazolidine
• 英文别名: tert-butyl (4S,5R)-4-[methoxy(methyl)carbamoyl]-2,2-dimethyl-5-propan-2-yl-1,3-oxazolidine-3-carboxylate
• CAS: 163625-43-2
• 化学式: C₁₆H₃₀N₂O₅
• 分子量: 330.425
• InChiKey: LZECCTFEIHWHLD-NWDGAFQWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  68.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4S,5R)-3-(tert-Butoxycarbonyl)-2,2-dimethyl-5-isopropyl-4-(N-methoxy-N-methylcarbamoyl)oxazolidine 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 0.33h， 以95%的产率得到(4S,5R)-3-(tert-Butoxycarbonyl)-2,2-dimethyl-4-formyl-5-isopropyloxazolidine
  参考文献：
  名称：

  Gold(I)-Catalyzed Asymmetric Aldol Reaction of N-Methoxy-N-methyl-.alpha.-isocyanoacetamide (.alpha.-Isocyano Weinreb Amide). An Efficient Synthesis of Optically Active .beta.-Hydroxy .alpha.-Amino Aldehydes and Ketones

  摘要：

  Asymmetric aldol reaction of N-methoxy-N-methyl-alpha-isocyanoacetamide (alpha-isocyano Weinreb amide) with aldehydes [RCHO: R = Ph, Me, i-Pr, (E)-MeCH=CH, (E)-BnOCH(2)CH=CH] in the presence of a gold(I) catalyst prepared in situ from [Au(c-HexNC)(2)]BF4 and chiral ferrocenylphosphine ligand (R)-N-methyl-N-(2-morpholinoethyl)-1-[(S)-1',2-bis(diphenylphosphino)ferrocenyl]ethylamine gave high yields of optically active trans-5-alkyl-2-oxazoline-4-(N-methoxy-N-methylcarboxamides) with high diastereo- and enantioselectivities. The diastereoselectivities (trans:cis) and enantiomeric excesses of the trans-oxazolines for the reaction with 1 mol % of the catalyst are as follows: R = Ph, 97:3, 96% ee; R = Me, 95:5, 97% ee; R = i-Pr, 98:2, 97% ee; R = (E)-MeCH=CH, 97:3; 99% ee; (E)-BnOCH(2)CH=CH, 96:4, 95% ee. These optically active oxazolines were converted to N,O-protected beta-hydroxy-alpha-amino aldehydes and ketone in high yields. An N-protected alpha-amino aldehyde (R = Ph) lacking the beta-hydroxyl group was also obtained through the catalytic hydrogenolysis of the oxazoline.

  DOI：

  10.1021/jo00111a034
• 作为产物：
  描述：

  (2S,3R)-2-Amino-3-hydroxy-4-methyl-pentanoic acid methoxy-methyl-amide 在 对甲苯磺酸 、 三乙胺 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 0.5h， 生成 (4S,5R)-3-(tert-Butoxycarbonyl)-2,2-dimethyl-5-isopropyl-4-(N-methoxy-N-methylcarbamoyl)oxazolidine
  参考文献：
  名称：

  Gold(I)-Catalyzed Asymmetric Aldol Reaction of N-Methoxy-N-methyl-.alpha.-isocyanoacetamide (.alpha.-Isocyano Weinreb Amide). An Efficient Synthesis of Optically Active .beta.-Hydroxy .alpha.-Amino Aldehydes and Ketones

  摘要：

  Asymmetric aldol reaction of N-methoxy-N-methyl-alpha-isocyanoacetamide (alpha-isocyano Weinreb amide) with aldehydes [RCHO: R = Ph, Me, i-Pr, (E)-MeCH=CH, (E)-BnOCH(2)CH=CH] in the presence of a gold(I) catalyst prepared in situ from [Au(c-HexNC)(2)]BF4 and chiral ferrocenylphosphine ligand (R)-N-methyl-N-(2-morpholinoethyl)-1-[(S)-1',2-bis(diphenylphosphino)ferrocenyl]ethylamine gave high yields of optically active trans-5-alkyl-2-oxazoline-4-(N-methoxy-N-methylcarboxamides) with high diastereo- and enantioselectivities. The diastereoselectivities (trans:cis) and enantiomeric excesses of the trans-oxazolines for the reaction with 1 mol % of the catalyst are as follows: R = Ph, 97:3, 96% ee; R = Me, 95:5, 97% ee; R = i-Pr, 98:2, 97% ee; R = (E)-MeCH=CH, 97:3; 99% ee; (E)-BnOCH(2)CH=CH, 96:4, 95% ee. These optically active oxazolines were converted to N,O-protected beta-hydroxy-alpha-amino aldehydes and ketone in high yields. An N-protected alpha-amino aldehyde (R = Ph) lacking the beta-hydroxyl group was also obtained through the catalytic hydrogenolysis of the oxazoline.

  DOI：

  10.1021/jo00111a034