(S)-1-((4S,5S)-4,5-Bis-tert-butoxymethyl-2-methyl-[1,3]dioxolan-2-yl)-ethylamine | 202280-09-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-1-((4S,5S)-4,5-Bis-tert-butoxymethyl-2-methyl-[1,3]dioxolan-2-yl)-ethylamine
• 英文别名: (1S)-1-[(4S,5S)-2-methyl-4,5-bis[(2-methylpropan-2-yl)oxymethyl]-1,3-dioxolan-2-yl]ethanamine
• CAS: 202280-09-9
• 化学式: C₁₆H₃₃NO₄
• 分子量: 303.442
• InChiKey: SFOCFHMRMXFFPL-AVGNSLFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  62.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  苯酐 、 (S)-1-((4S,5S)-4,5-Bis-tert-butoxymethyl-2-methyl-[1,3]dioxolan-2-yl)-ethylamine 在 sodium acetate 作用下， 生成 2-[(S)-1-((4S,5S)-4,5-Bis-tert-butoxymethyl-2-methyl-[1,3]dioxolan-2-yl)-ethyl]-isoindole-1,3-dione
  参考文献：
  名称：

  1,4-Di-O-tert-alkyl-l-threitols as Chiral Auxiliaries in the Asymmetric Nucleophilic Addition of Alkyllithiums to Hydrazones

  摘要：

  The applications of 1,4-di-O-tert-alkyl-L-threitols as chiral auxiliaries in the asymmetric nucleophilic addition of alkyllithiums to hydrazones are investigated. Chiral acetal-hydrazones 9, obtained from the chiral acetals 8 by ozonolysis followed by treatment with dimethylhydrazine, are allowed to react with organolithium reagents in toluene at -78 degrees C to give 15 with excellent diastereoselectivity. The stereochemical assignments were based an the X-ray crystal structure of 17a. The absolute configuration at C-2 Of the major isomer of the adducts 15 was thereby determined to be S. The nucleophile thus attacked from the si face of the C=N moiety. The effect of solvent on the diastereoselectivity of the reactions of 9 with organolithium reagents is reported. Polar aprotic solvent shows poor diastereoselectivity, and the diastereoselectivity; is reversed when the reaction is carried out in THF. Reaction of dl-14 with methyllithium has been studied for comparison purposes and the reaction shows the opposite selectivity. Chelation intermediates 18 and 26 are proposed for these reactions to account for the observed stereoselectivities.

  DOI：

  10.1021/jo971700y
• 作为产物：
  描述：

  (2S,3S)-1,4-Di-tert-butoxy-butane-2,3-diol 在 二甲基硫 、 Ranei Ni 、 4-甲基苯磺酸吡啶 、 臭氧 作用下， 以 甲醇 、 甲苯 、 苯 为溶剂， 生成 (S)-1-((4S,5S)-4,5-Bis-tert-butoxymethyl-2-methyl-[1,3]dioxolan-2-yl)-ethylamine
  参考文献：
  名称：

  1,4-Di-O-tert-alkyl-l-threitols as Chiral Auxiliaries in the Asymmetric Nucleophilic Addition of Alkyllithiums to Hydrazones

  摘要：

  The applications of 1,4-di-O-tert-alkyl-L-threitols as chiral auxiliaries in the asymmetric nucleophilic addition of alkyllithiums to hydrazones are investigated. Chiral acetal-hydrazones 9, obtained from the chiral acetals 8 by ozonolysis followed by treatment with dimethylhydrazine, are allowed to react with organolithium reagents in toluene at -78 degrees C to give 15 with excellent diastereoselectivity. The stereochemical assignments were based an the X-ray crystal structure of 17a. The absolute configuration at C-2 Of the major isomer of the adducts 15 was thereby determined to be S. The nucleophile thus attacked from the si face of the C=N moiety. The effect of solvent on the diastereoselectivity of the reactions of 9 with organolithium reagents is reported. Polar aprotic solvent shows poor diastereoselectivity, and the diastereoselectivity; is reversed when the reaction is carried out in THF. Reaction of dl-14 with methyllithium has been studied for comparison purposes and the reaction shows the opposite selectivity. Chelation intermediates 18 and 26 are proposed for these reactions to account for the observed stereoselectivities.

  DOI：

  10.1021/jo971700y

文献信息

• 1,4-Di-<i>O-tert-</i>alkyl-<scp>l</scp>-threitols as Chiral Auxiliaries in the Asymmetric Nucleophilic Addition of Alkyllithiums to Hydrazones
  作者：Yu-Tsai Hsieh、Gene-Hsiang Lee、Yu Wang、Tien-Yau Luh

  DOI：10.1021/jo971700y

  日期：1998.3.1

  The applications of 1,4-di-O-tert-alkyl-L-threitols as chiral auxiliaries in the asymmetric nucleophilic addition of alkyllithiums to hydrazones are investigated. Chiral acetal-hydrazones 9, obtained from the chiral acetals 8 by ozonolysis followed by treatment with dimethylhydrazine, are allowed to react with organolithium reagents in toluene at -78 degrees C to give 15 with excellent diastereoselectivity. The stereochemical assignments were based an the X-ray crystal structure of 17a. The absolute configuration at C-2 Of the major isomer of the adducts 15 was thereby determined to be S. The nucleophile thus attacked from the si face of the C=N moiety. The effect of solvent on the diastereoselectivity of the reactions of 9 with organolithium reagents is reported. Polar aprotic solvent shows poor diastereoselectivity, and the diastereoselectivity; is reversed when the reaction is carried out in THF. Reaction of dl-14 with methyllithium has been studied for comparison purposes and the reaction shows the opposite selectivity. Chelation intermediates 18 and 26 are proposed for these reactions to account for the observed stereoselectivities.