Department of Chemistry, University of Bath, Claverton Down, Bath, BA2 7AY, UK.
Chem Soc Rev. 2010 Jun;39(6):2093-105. doi: 10.1039/b919762c. Epub 2010 Apr 21.
The rhodium catalysed conjugate addition of organometallics to activated alkenes is a powerful synthetic tool for establishing new carbon-carbon bonds often with high stereoselectivity. The introduction of a practical, efficient method for introducing functionalised aryl and alkenyl fragments with predictable stereocontrol has caught the attention of synthetic chemists and emerging examples are growing in number and complexity. In this tutorial review, we document notable advances in the application of rhodium catalysed conjugate addition processes within the context of synthesis of complex molecules and intermediates in drug discovery. The chosen examples illustrate important issues regarding scope, selectivity and reactivity that will help guide the selection of appropriate donor and acceptor to achieve the desired carbon-carbon bond construction when planning new synthetic routes.
铑催化的有机金属与活化烯烃的共轭加成是建立新的碳-碳键的有力合成工具,通常具有高立体选择性。引入一种实用、高效的方法,可引入具有可预测立体控制的官能化芳基和烯基片段,引起了合成化学家的关注,并且越来越多的实例在数量和复杂性上不断增加。在本综述中,我们记录了铑催化的共轭加成过程在复杂分子和药物发现中的中间体制备中的应用的显著进展。所选择的例子说明了关于范围、选择性和反应性的重要问题,这些问题将有助于指导在规划新的合成路线时选择合适的供体和受体以实现所需的碳-碳键构建。