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3,3′-Bithiophene-Based Chiral Bisphosphine Oxides as Organocatalysts in Silicon-Derived Lewis Acid Mediated Reactions
Synlett ( IF 1.7 ) Pub Date : 2020-01-07 , DOI: 10.1055/s-0039-1690777 Sergio Rossi 1 , Tiziana Benincori 2 , Laura Maria Raimondi 1 , Maurizio Benaglia 1
Synlett ( IF 1.7 ) Pub Date : 2020-01-07 , DOI: 10.1055/s-0039-1690777 Sergio Rossi 1 , Tiziana Benincori 2 , Laura Maria Raimondi 1 , Maurizio Benaglia 1
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This account summarizes the development of new biheteroaromatic chiral bisphosphine oxides. 3,3′-Bithiophene-based phosphine oxides (BITIOPOs) have been successfully used as organocatalysts to promote Lewis base catalyzed, Lewis acid mediated stereoselective transformations. These highly electron-rich compounds, in combination with trichorosilyl derivatives (allyltrichlorosilane and silicon tetrachloride), generate hypervalent silicon species that act as chiral Lewis acids in highly diastereo- and enantioselective organic reactions. Several relevant examples related to these applications are discussed in detail. 1 Introduction 2 The BITIOPO Family 3 Enantioselective Opening of Epoxides 4 Enantioselective Allylation of Aldehydes 5 Stereoselective Direct (Double) Aldol-Type Reaction with Ketones 6 Stereoselective Direct Aldol-Type Reaction with Ester Derivatives 7 Conclusions
中文翻译：
3,3'-联噻吩基手性双膦氧化物在硅衍生的路易斯酸介导反应中作为有机催化剂
该帐户总结了新的双杂芳族手性双膦氧化物的开发。3,3'-联噻吩基氧化膦 (BITIOPO) 已成功用作有机催化剂，以促进路易斯碱催化、路易斯酸介导的立体选择性转化。这些高度富电子的化合物与三氯甲硅烷基衍生物（烯丙基三氯硅烷和四氯化硅）结合，生成高价硅物质，在高度非对映选择性和对映选择性有机反应中充当手性路易斯酸。详细讨论了与这些应用程序相关的几个相关示例。
更新日期：2020-01-07
中文翻译：
3,3'-联噻吩基手性双膦氧化物在硅衍生的路易斯酸介导反应中作为有机催化剂
该帐户总结了新的双杂芳族手性双膦氧化物的开发。3,3'-联噻吩基氧化膦 (BITIOPO) 已成功用作有机催化剂，以促进路易斯碱催化、路易斯酸介导的立体选择性转化。这些高度富电子的化合物与三氯甲硅烷基衍生物（烯丙基三氯硅烷和四氯化硅）结合，生成高价硅物质，在高度非对映选择性和对映选择性有机反应中充当手性路易斯酸。详细讨论了与这些应用程序相关的几个相关示例。
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