Domino Reactions Involving Catalytic Enantioselective Conjugate Additions
Domino Reactions Involving Catalytic Enantioselective Conjugate Additions
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涉及催化对映选择性共轭加成的多米诺反应
DOI：
10.1002/9783527630578.ch8
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发表时间：
2010
期刊：
影响因子：
--
通讯作者：
Alexander Duefert
中科院分区：
文献类型：
--
作者：
L. Tietze;Alexander Duefert
在现代合成化学中，非常需要开发新的方法，从简单的底物开始，在几个步骤中有效地形成复杂的结构。此外，必须寻求新的方法来减轻环境负担和保护自然资源。然而，这些新的合成方法必须结合经济优势，以便它们可以被工业用于开发和生产领域。在过去的几年里，多米诺骨牌反应--被定义为……在相同的反应条件下，两个或多个成键反应的过程，其中后一种转化发生在前一种成键反应中获得的官能团……[1]，在合成有机化学中显示出巨大的潜力。这些反应代表了一种新的合成概念，能够从简单的底物开始有效地制备复杂化合物。此外，这种反应在经济和生态上都是有益的，因为它们不仅可以减少废物的产生，而且还可以保证勤奋地利用地球资源。在这一章中，描述了α，β-不饱和羰基化合物的对映选择性多米诺-1，4-加成反应，然后与电泳剂或另一种转化反应。亲核剂1，4-加成到α，β-不饱和的醛、酮和羧酸的衍生物上，然后用亲电性截留中间形成的烯醇，这代表了一个众所周知的和高度成熟的合成过程。然而，文献中已经报道了许多手性底物的非对映选择性Michael加成反应的细节，但在手性催化剂--无论是过渡金属还是有机催化剂--控制下的1，4-对映选择性加成反应要少得多，而且是最近才建立的。这种“新”方法不仅被用于小分子的合成，而且在几种天然产物的对映选择性全合成中也展示了它的多功能性。已经开发了两种不同的方法，这两种方法都允许引入具有良好对映体过量(Ee)值的第一个立体中心；
In modern synthetic chemistry, there is a great need for the development of new procedures that will allow the efficient formation of complex structures in a few steps, starting from simple substrates. Moreover, new ways must be sought to reduce the burden on the environment and to conserve natural resources. Yet, these new synthetic procedures methods must incorporate economic advantages such that they can be used by industry in areas of both development and production. Over the past years, domino reactions–which are defined as ‘‘... processes of two or more bond-forming reactions under identical reaction conditions, in which the latter transformations take place at the functionalities obtained in the former bond-forming reactions...’’[1] have demonstrated their huge potential in synthetic organic chemistry. These reactions represent a novel concept in synthesis that enables the efficient preparation of complex compounds, starting from simple substrates. Moreover, such reactions are economically and ecologically beneficial, as they not only allow reductions to be made in the generation of waste materials, but also guarantee a diligent conduct with the Earth’s resources. In this chapter, a description is provided of the enantioselective domino-1, 4-addition to α, β-unsaturated carbonyl compounds, followed by reaction with an electrophile or another transformation. The 1, 4-addition of nucleophiles to α, β-unsaturated aldehydes, ketones, and carboxylic acid derivatives, followed by an interception of the intermediately formed enolate with electrophiles, represents a well-known and highly established synthetic procedure. Whereas, the details of many diastereoselective Michael additions of chiral substrates have been reported in the literature, enantioselective 1, 4-additions under the control of a chiral catalyst–whether a transition metal or an organocatalyst–are much less common and have been established only relatively recently [2]. This ‘‘new’’approach has been used not only for the creation of small molecules; rather, it has also demonstrated its versatility in the enantioselective total synthesis of several natural products. Two different procedures have been developed, both of which allow the introduction of a first stereocenter with excellent enantiomeric excess (ee)-values;
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