基于异氰基乙酸乙酯与多取代二乙烯基酮的新型串联反应研究
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摘要
当前,社会的可持续性发展及其所涉及的生态、环境、资源、经济等方面的问题已经成为国际社会关注的焦点。如何从源头上消除或减少废物排放对有机合成而言是极具挑战性的研究课题。串联反应是一种“一个反应瓶”内进行的多步反应,反应连续、有序地进行,不经中间产物的分离直接得到最终产物。由于避免了中间产物的分离纯化步骤,从而大大节省了试剂用量和时间,具有高效和环境友好等优点,得到了有机化学家的广泛关注。
本论本致力于发展新颖、高效的多步串联反应。以含有多个反应位点的异氰基乙酸乙酯和多取代二乙烯基酮为底物,通过多步的串联反应简洁地构筑具有生物活性的吡咯并环和桥环化合物,为吡咯里西啶和6-氮杂双环[3.2.1]辛烷等化合物提供了新的合成方法。同时对所涉及的反应机理进行了深入研究。
本论文共分为五章,前两章为论文的背景与选题,综述了近几十年来串联反应的研究进展与异腈化学的发展,在此基础上结合本课题组的研究工作提出了选题依据。
第三章描述了利用有机小分子催化的四步串联反应合成吡咯里西啶类化合物的新策略。在1,8-二氮杂双环[5.4.0]十一碳-7-烯(DBU)的催化下,异氰基乙酸乙酯和多取代二乙烯基酮发生串联的双迈克尔加成/分子内环合/1,3-酰基转移反应,高选择性地合成了多官能团化的吡咯里西啶类化合物。根据捕捉的中间体结构,提出了可能的反应机理。该反应提供了一种由开链化合物出发“一锅”合成吡咯里西啶双环体系的新方法。
第四章阐述了利用有机小分子催化的三步串联反应合成6-氮杂双环[3.2.1]辛烷类化合物的新方法。在DBU的催化下,异氰基乙酸乙酯和2-芳基或烷基取代的二乙烯基酮发生串联的双迈克尔加成/分子内环合反应,立体选择性地合成了多官能团化的6-氮杂双环[3.2.1]辛烷类化合物。
第五章论述了α-芳甲酰基-α-烯酰基二硫缩烯酮与异氰基乙酸乙酯的串联迈克尔加成/1,3-偶极环加成反应,立体选择性地合成了多官能团化的六氢苯并噁唑类化合物。
本论本中所涉及的异氰基乙酸乙酯参与的串联反应有以下特点:(1)机理新颖;(2)效率高,在“一锅”反应中形成了多个化学键和两个环;(3)可生成四个相邻的手性中心;(4)原子利用率达到了100%;(5)高区域选择性和非对映异构选择性。所发展的合成策略为吡咯里西啶,6-氮-双环[3.2.1]辛烷等具有天然产物母核结构的生物活性化合物以及六氢苯并噁唑类化合物等“类天然产物”的合成提供了一种简单、高效、易操作、条件温和且绿色环保的合成方法。
Tandem reactions, which result from the combination of multiple transformations in a single pot, could efficiently afford complex products from simple, readily available starting materials. Such processes are both economically and ecologically beneficial and environmentally benign, which could minimize the requisite reagents, solvents, costs, time, and separation processes for the desired transformation and also minimize the formation of waste. Therefore, the development of novel tandem reactions is particularly attractive in modern organic chemistry.
This dissertation is devoted to develop novel strategies for the construction of biologically active fused and -bridged pyrrole compounds through highly efficient multisteps tandem reactions between isocyanoacatate and 1,4-dien-3-ones. Mechanisms of these new reactions were also investigated in details.
The dissertation is divided into five chapters. In chapter one, the progresses on both tandem reactions and isocyanide chemistry were reviewed. Based on chapter one and combined with our group’s research works, the dissertation proposal was presented.
Chapter three describes a novel strategy for the synthesis of pyrrolizidines through an organocatalytic quadruple tandem reaction. Catalyzed by DBU, polyfunctionalized pyrrolizidines were stereoselectively constructed by a tandem double-Michael-addition/cyclization/acyl migration of 1,4-dien-3-ones and ethyl isocyanoacetate. A possible mechanism of this reaction is proposed based on the isolated intermediates.
Chapter four involves a novel strategy for the synthesis of 6-azabicyclo[3.2.1]octanes by an organocatalytic triple domino reaction. Catalyzed by DBU, polyfunctionalized 6-azabicyclo[3.2.1]octanes with up to five adjacent stereocenters were stereoselectively constructed by a tandem double-Michael -addition/cyclization of 1,4-dien-3-ones and ethyl isocyanoacetate.
Chapter five shows a new strategy for the stereoselective synthesis of 4,5,7,7a-tetrahydrobenzo[d]oxazol-6(3aH)-ones by tandem Michael addition/1,3- dipolar cycloaddition reactions ofα-alkenoyl-α-benzoyl ketene-(S,S)-acetals and isocyanoacetate.
The benefits of the tandem reactions in this dissertation are summarized as below: (1) novel mechanism; (2) high efficiency, up to four bonds and two rings were formed in one-pot operation; (3) up to four adjacent stereocenters were formed; (4) perfectly atom-economy; (5) excellent regio- and diastereoselectivity. The studies in this dissertation discovered novel and efficient domino reactions to form azabicyclic skeleton, found in natural alkaloids, and paved the way to synthesis such natural-like product libraries under simple, mild and environmentally benign conditions.
本论本致力于发展新颖、高效的多步串联反应。以含有多个反应位点的异氰基乙酸乙酯和多取代二乙烯基酮为底物,通过多步的串联反应简洁地构筑具有生物活性的吡咯并环和桥环化合物,为吡咯里西啶和6-氮杂双环[3.2.1]辛烷等化合物提供了新的合成方法。同时对所涉及的反应机理进行了深入研究。
本论文共分为五章,前两章为论文的背景与选题,综述了近几十年来串联反应的研究进展与异腈化学的发展,在此基础上结合本课题组的研究工作提出了选题依据。
第三章描述了利用有机小分子催化的四步串联反应合成吡咯里西啶类化合物的新策略。在1,8-二氮杂双环[5.4.0]十一碳-7-烯(DBU)的催化下,异氰基乙酸乙酯和多取代二乙烯基酮发生串联的双迈克尔加成/分子内环合/1,3-酰基转移反应,高选择性地合成了多官能团化的吡咯里西啶类化合物。根据捕捉的中间体结构,提出了可能的反应机理。该反应提供了一种由开链化合物出发“一锅”合成吡咯里西啶双环体系的新方法。
第四章阐述了利用有机小分子催化的三步串联反应合成6-氮杂双环[3.2.1]辛烷类化合物的新方法。在DBU的催化下,异氰基乙酸乙酯和2-芳基或烷基取代的二乙烯基酮发生串联的双迈克尔加成/分子内环合反应,立体选择性地合成了多官能团化的6-氮杂双环[3.2.1]辛烷类化合物。
第五章论述了α-芳甲酰基-α-烯酰基二硫缩烯酮与异氰基乙酸乙酯的串联迈克尔加成/1,3-偶极环加成反应,立体选择性地合成了多官能团化的六氢苯并噁唑类化合物。
本论本中所涉及的异氰基乙酸乙酯参与的串联反应有以下特点:(1)机理新颖;(2)效率高,在“一锅”反应中形成了多个化学键和两个环;(3)可生成四个相邻的手性中心;(4)原子利用率达到了100%;(5)高区域选择性和非对映异构选择性。所发展的合成策略为吡咯里西啶,6-氮-双环[3.2.1]辛烷等具有天然产物母核结构的生物活性化合物以及六氢苯并噁唑类化合物等“类天然产物”的合成提供了一种简单、高效、易操作、条件温和且绿色环保的合成方法。
Tandem reactions, which result from the combination of multiple transformations in a single pot, could efficiently afford complex products from simple, readily available starting materials. Such processes are both economically and ecologically beneficial and environmentally benign, which could minimize the requisite reagents, solvents, costs, time, and separation processes for the desired transformation and also minimize the formation of waste. Therefore, the development of novel tandem reactions is particularly attractive in modern organic chemistry.
This dissertation is devoted to develop novel strategies for the construction of biologically active fused and -bridged pyrrole compounds through highly efficient multisteps tandem reactions between isocyanoacatate and 1,4-dien-3-ones. Mechanisms of these new reactions were also investigated in details.
The dissertation is divided into five chapters. In chapter one, the progresses on both tandem reactions and isocyanide chemistry were reviewed. Based on chapter one and combined with our group’s research works, the dissertation proposal was presented.
Chapter three describes a novel strategy for the synthesis of pyrrolizidines through an organocatalytic quadruple tandem reaction. Catalyzed by DBU, polyfunctionalized pyrrolizidines were stereoselectively constructed by a tandem double-Michael-addition/cyclization/acyl migration of 1,4-dien-3-ones and ethyl isocyanoacetate. A possible mechanism of this reaction is proposed based on the isolated intermediates.
Chapter four involves a novel strategy for the synthesis of 6-azabicyclo[3.2.1]octanes by an organocatalytic triple domino reaction. Catalyzed by DBU, polyfunctionalized 6-azabicyclo[3.2.1]octanes with up to five adjacent stereocenters were stereoselectively constructed by a tandem double-Michael -addition/cyclization of 1,4-dien-3-ones and ethyl isocyanoacetate.
Chapter five shows a new strategy for the stereoselective synthesis of 4,5,7,7a-tetrahydrobenzo[d]oxazol-6(3aH)-ones by tandem Michael addition/1,3- dipolar cycloaddition reactions ofα-alkenoyl-α-benzoyl ketene-(S,S)-acetals and isocyanoacetate.
The benefits of the tandem reactions in this dissertation are summarized as below: (1) novel mechanism; (2) high efficiency, up to four bonds and two rings were formed in one-pot operation; (3) up to four adjacent stereocenters were formed; (4) perfectly atom-economy; (5) excellent regio- and diastereoselectivity. The studies in this dissertation discovered novel and efficient domino reactions to form azabicyclic skeleton, found in natural alkaloids, and paved the way to synthesis such natural-like product libraries under simple, mild and environmentally benign conditions.
引文
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