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Development of A Chiral Homoenolate Equivalent which Reacts Selectively with Imines

Development of A Chiral Homoenolate Equivalent which Reacts Selectively with Imines
开发与亚胺选择性反应的手性高烯醇等价物
批准号:
12650847
负责人:
OKAMOTO Sentaro
金额:
$2.37万
依托单位国家:
日本
项目类别:
Grant-in-Aid for Scientific Research (C)
财政年份:
2000
资助国家:
日本
项目状态:
已结题
起止时间:
2000 至 2001

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中文摘要
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英文摘要
A chiral allyltitanium compound, prepared in situ by the reaction of optically active acrolein 1,2-dicyclohexylethylene acetal with a divalent titanium reagent, Ti(O-i-Pr)_4/2i-PrMgCl, reacts with a variety of acyclic and cyclic imines in a regiospecific way to afford cc-addition products as a mixture of the E- and Z-isomers in good combined yield, where the former is predominant in a ratio of 92:8 to >95:5. The mixture of (E)- and (Z)-adducts and pure (E)-adducts which could be isolated in several cases were respectively converted to the corresponding β-amino esters to confirm the absolute configuration and enantiomeric purity. The ee of the newly-formed asymmetric center is more than 78 % for the mixture of (E)- and (Z)-addition products and more than 96 % for pure (E)-isomer. By taking advantage of the versatility of the vinyl ether moiety in reaction products, optically active γ-amino aldehydes, γ-amino aldehyde acetals, y-amino acids, β-amino esters, andpyrrolidinoisoquinolines were readily prepared. In the reaction of the allyltitanium with optically active cc-silyloxyimine, remarkable double stereodifferentiation was observed; thus, the reaction of the allyltitanium derived from (S,S)- or (R,R)-1,2-dicyclohexylethylene acetal provided syn- and anti-adducts in a ratio of 55 : 45 or 0 : 100 respectively. Meanwhile, the stereochemistry of the product in the reaction with β-silyloxyimine was controlled mainly by the allyltitanium. The reaction could be effectively applied to prepare 4-amino-6-hydroxypentadecanal dimethyl acetal, a key intermediate for the synthesis of batzelladine D.
期刊论文(24)
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会议论文
Sentaro Okamoto: "Titanium (IV) Aryloxide Catalyzed Cyclization Reactions of 1,6-and 1,7-Dienes"J.Am.Chem.Soc.. 122. 1223-1224 (2000)
Sentaro Okamoto:“钛 (IV) 芳基氧化物催化 1,6-和 1,7-二烯的环化反应”J.Am.Chem.Soc.. 122. 1223-1224 (2000)
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Sentaro Okamoto, Fumie Sato: "A Highly Efficient and Practical Preparation of 2,4-Pentadienyltitaniums and their γ-Selective Addition Reaction with Aldehydes and Ketones"J. Organomet. Chem.. 624. 151-156 (2001)
Sentaro Okamoto、Fumie Sato:“2,4-戊二烯基钛的高效实用制备及其与醛和酮的 γ-选择性加成反应”J. Organomet. 624. 151-156 (2001)
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Sentaro Okamoto: "An Efficient and Practical Preparation of Optically Active syn-1-Vinyl-2-amino Alcohol Derivatives by the Regio-and Diastereoselective Addition Reaction of (γ-Alkoxyallyl) titaniums with Chiral Imines.Formal Synthesis of Statine"Tetrahed
Sentaro Okamoto:“通过(γ-烷氧基烯丙基)钛与手性亚胺的区域和非对映选择性加成反应,高效实用地制备光学活性 syn-1-Vinyl-2-amino 醇衍生物。他汀的正式合成”
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Sentaro Okamoto: "General synthetic method for preparation of optically active propargyl and allenylstannanes"Tetrahedron Letters. 42. 6323-6326 (2001)
Sentaro Okamoto:“制备光学活性炔丙基和联烯基锡烷的通用合成方法”Tetrahedron Letters。
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22
    Development of Cleavage Reactions of C-O and N-S Bonds Promoted by Novel Low-Valent Titanium Reagents and Their Synthetic Applications
    • 批准号:
      22550103
    • 项目类别:
      Grant-in-Aid for Scientific Research (C)
    • 资助金额:
      $3.08万
    • 财政年份:
      2010
    • 负责人:
      OKAMOTO Sentaro
    • 依托单位:
    New Low Valent Titanium Reagents and Their Application to Bond-Forming and-Cleaving Reactions
    • 批准号:
      19550113
    • 项目类别:
      Grant-in-Aid for Scientific Research (C)
    • 资助金额:
      $3.08万
    • 财政年份:
      2007
    • 负责人:
      OKAMOTO Sentaro
    • 依托单位:
    Stereoselective Synthesis of a-Branched Amines Based on Formation of Azatitanacyclic Compounds
    • 批准号:
      16550102
    • 项目类别:
      Grant-in-Aid for Scientific Research (C)
    • 资助金额:
      $2.37万
    • 财政年份:
      2004
    • 负责人:
      OKAMOTO Sentaro
    • 依托单位:
    Tandem Inter-/intramolecular Coupling Mediated by a Ti(II) Reagent : One-step Multibond-forming Reactions
    • 批准号:
      14550819
    • 项目类别:
      Grant-in-Aid for Scientific Research (C)
    • 资助金额:
      $2.24万
    • 财政年份:
      2002
    • 负责人:
      OKAMOTO Sentaro
    • 依托单位:
    海外基金