(2S,4R,5R)-3-(Benzenesulfonyl)-4-(2-hydroxyethyl)-5-methyldihydrofuran-2-one | 142968-38-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S,4R,5R)-3-(Benzenesulfonyl)-4-(2-hydroxyethyl)-5-methyldihydrofuran-2-one
• CAS: 142968-38-5
• 化学式: C₁₃H₁₆O₅S
• 分子量: 284.333
• InChiKey: RKZSZYZCOHPXTR-JLLWLGSASA-N

反应信息

• 作为反应物：
  描述：

  甲基磺酰氯 、 (2S,4R,5R)-3-(Benzenesulfonyl)-4-(2-hydroxyethyl)-5-methyldihydrofuran-2-one 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以96%的产率得到2-<(2R,3R,4S)-4-(Benzenesulfonyl)-2-methyl-5-oxotetrahydrofuran-3-yl>ethyl methanesulfonate
  参考文献：
  名称：

  Stereoselective Synthesis of Highly Substituted .gamma.-Lactones by Diastereoselective Alkylation of .alpha.-(Benzenesulfonyl) Derivatives with Unusual Facial Selectivity

  摘要：

  The oxidation of alpha-(phenylthio) gamma-lactones obtained by the base-induced cyclization of enantiomerically enriched gamma-[(phenylthio) acyl]-alpha,beta-unsaturated esters to sulfones in those cases where the a-carbon has an available proton and further basic alkylation led to an unexpected facial selectivity. The reaction proceeded smoothly with alkylating agents and unsaturated carbonyl compounds, but was unsuccessful when an addition to carbonyl derivatives was attempted. The alkylation reaction was performed over a wide range of substituted substrates in order to investigate the scope and limitations of the method and to have information about the possible origin of the selectivity. The application of the alkylation reaction was extended to the synthesis of bicyclic systems, including a cyclobutane with total stereochemical control. The presence of the alpha-(benzenesulfonyl) group is shown to be essential to achieve the facial selection. In order to rationalize the stereochemical results, extensive semiempirical calculations were performed. The use of MNDO and AM1 permits rationalization of the fact that the alpha-(benzenesulfonyl) group encumbers a diastereoface of the enolate generated in the ring, leading to the observed stereochemistry.

  DOI：

  10.1021/jo00105a027
• 作为产物：
  描述：

  (2R,3R,4S)-<4-(Benzenesulfonyl)-2-methyl-5-oxotetrahydrofuran-3-yl>acetic acid 在 dimethyl sulfide borane 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 以88%的产率得到(2S,4R,5R)-3-(Benzenesulfonyl)-4-(2-hydroxyethyl)-5-methyldihydrofuran-2-one
  参考文献：
  名称：

  Stereoselective Synthesis of Highly Substituted .gamma.-Lactones by Diastereoselective Alkylation of .alpha.-(Benzenesulfonyl) Derivatives with Unusual Facial Selectivity

  摘要：

  The oxidation of alpha-(phenylthio) gamma-lactones obtained by the base-induced cyclization of enantiomerically enriched gamma-[(phenylthio) acyl]-alpha,beta-unsaturated esters to sulfones in those cases where the a-carbon has an available proton and further basic alkylation led to an unexpected facial selectivity. The reaction proceeded smoothly with alkylating agents and unsaturated carbonyl compounds, but was unsuccessful when an addition to carbonyl derivatives was attempted. The alkylation reaction was performed over a wide range of substituted substrates in order to investigate the scope and limitations of the method and to have information about the possible origin of the selectivity. The application of the alkylation reaction was extended to the synthesis of bicyclic systems, including a cyclobutane with total stereochemical control. The presence of the alpha-(benzenesulfonyl) group is shown to be essential to achieve the facial selection. In order to rationalize the stereochemical results, extensive semiempirical calculations were performed. The use of MNDO and AM1 permits rationalization of the fact that the alpha-(benzenesulfonyl) group encumbers a diastereoface of the enolate generated in the ring, leading to the observed stereochemistry.

  DOI：

  10.1021/jo00105a027

文献信息

• An example of a chiral non-racemic carbanion as versatile synthon in the asymmetric synthesis of polysubstituted γ-lactones
  作者：Carmen Ma Rodríguez、Miguel A. Ramírez、Victor S. Martín

  DOI：10.1016/s0040-4039(00)79594-3

  日期：1992.5

  The application of a chiral non-racemic carbanion generated from enantiomerically enriched α-sulfonyl-γ-lactones to the asymmetric synthesis of highly substituted and fused γ-lactones is described.

  描述了由对映异构体富集的α-磺酰基-γ-内酯产生的手性非外消旋碳负离子在高度取代和稠合的γ-内酯的不对称合成中的应用。