Asymmetric Automultiplication of Chiral Compounds by Asymmetric Autocatalytic Reaction

不对称自催化反应手性化合物的不对称自倍增

• 批准号: 07454168
• 负责人: SOAI Kenso
• 金额: $ 4.93万
• 依托单位: Science University of Tokyo
• 依托单位国家: 日本
• 项目类别: Grant-in-Aid for Scientific Research (B)
• 财政年份: 1995
• 资助国家: 日本
• 起止时间: 1995 至 1996
• 项目状态: 已结题
• 来源: https://kaken.nii.ac.jp/grant/KAKENHI-PROJECT-07454168/
• 关键词: Asymmetric autocatalysis; Dialkylzinc; Asymmetric automultiplication; Asymmetric replication; Pyrimidyl alkanol; Quinolyl alkanol; Asymmetric synthesis; 自己増殖; 不斉自己触媒反応; 不斉アルキル化反応; ピリミジルアルコール; キノリルアルコール

Asymmetric autocatalytic reaction of 2-methyl-1- (5-pyrimidyl) -1-propanol (1) was examined. (S) -1 with high e.e.worked as an asymmetric autocatalysis in the reaction of pyrimidine-5-carbaldehyde and diisopropylzinc to afford (S) -1 with high e.e. When (S) -1 with low e.e.was employed as an asymmetric autocatalyst, the newly formed (S) -1 had an higher e.e. By using the newly formed (S) -1 as the asymmetric autocatalyst for the next reaction, the e.e. of (S) -1 reached 90%e.e. Quinolyl alkanol is also an asymmetric autocatalysis to afford itself with 94% e.e.in the reaction of quinoline-3-carbaldehyde and diisopropylzinc.

检查了2-甲基-1-(5-嘧啶基)-1-丙醇(1)的不对称自催化反应。高e.e.的(S)-1在嘧啶-5-甲醛和二异丙基锌的反应中作为不对称自催化得到高e.e.的(S)-1。当低e.e.的(S) -1用作不对称自催化剂时，新形成的(S) -1具有较高的e.e.。通过使用新形成的(S) -1 作为下一步反应的不对称自催化剂，e.e. (S) -1 达到 90%e.e.喹啉基烷醇也是一种不对称自催化，在喹啉-3-甲醛和二异丙基锌的反应中产生 94% e.e.。

项目成果

K.Soai: "Asymmetric Synthesis of Chiral Diols by the Catalytic Enantioselective Dialkylation of Tere-,Iso-,and Phthalaldehydes and by a Catalytic Enantioselective Autoinductive Reaction." Tetrahedron. 52. 13355-13362 (1996)

K.Soai：“通过对映醛、异醛和邻苯二醛的催化对映选择性二烷基化以及催化对映选择性自诱导反应合成手性二醇。”

T.Shibata: "Asymmetric Synthesis of Various Chiral 5-Pyrimidylalkanols by the Enantioselective Alkylation of Pyrimidine-5-carbaldehydes with Dialkylzincs in the Presence of Chiral Amino Alcohols" Heterocycles. 46. 235-240 (1997)

T.Shibata：“在手性氨基醇存在下，通过嘧啶-5-甲醛与二烷基锌的对映选择性烷基化来不对称合成各种手性 5-嘧啶基烷醇”杂环。

そ合: "Asymmetric Autocatalysis and Amplification of Enantiomeric Excess of a chiral Mdecule" Nature. 378. 767-768 (1995)

Soai：“手性分子过量的不对称自催化和扩增”自然，378. 767-768 (1995)。

K.Soai: "Design of Chiral Catalysis and Asymmetric Autocatalysis for the Enantioselective Additions of Organozinc Reagents" Yuki Gosei Kagaku Kyokaishi. 55. 994-1005 (1997)

K.Soai：“有机锌试剂对映选择性加成的手性催化和不对称自催化设计”Yuki Gosei Kagaku Kyokaishi。

T.Shibata: "Highly Enantioselective Catalytic Asymmetric Automultiplication of Chiral Pyrimidylalcohol." J.Am.Chem.Soc.118. 471-472 (1996)

T.Shibata：“手性嘧啶醇的高度对映选择性催化不对称自倍增”。