Acetic acid (1S,2R)-1,2-bis-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-hydroxy-ethyl ester | 27949-83-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Acetic acid (1S,2R)-1,2-bis-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-hydroxy-ethyl ester
• CAS: 27949-83-3
• 化学式: C₁₄H₂₄O₇
• 分子量: 304.34
• InChiKey: TUTQBUDRWUWING-DDHJBXDOSA-N

反应信息

• 作为反应物：
  描述：

  Acetic acid (1S,2R)-1,2-bis-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-hydroxy-ethyl ester 在 草酰氯 、 TEA 、 二甲基亚砜 作用下， 以 二氯甲烷 为溶剂， 以83%的产率得到Acetic acid (R)-1,2-bis-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-oxo-ethyl ester
  参考文献：
  名称：

  Diastereoselective Grignard Additions to O-Protected Polyhydroxylated Ketones:  A Reaction Controlled by Groundstate Conformation?

  摘要：

  The O-protected polyhydroxy ketones 9-14 and 39, 42 add sigma-type Grignard reagents with >90:10 stereoselectivity to give the 3,4-syn-adducts 17-28 and 43, 45, respectively, as the major diastereomers (Tables 1 and 2). The stereoselectivity is interpreted in terms of early transition states which are very close to the groundstate conformations shown in Figure 6 and 7. These demonstrate that the ''top face'' of the carbonyl group is much less shielded than the ''bottom'' face. Complexation phenomena are of minor importance. It is also shown that the classical transition state models (Felkin-Anh or chelate Cram) are not applicable to polyoxygenated ketones.

  DOI：

  10.1021/jo961542v