Pichon Delphine, Morvan Jennifer, Crévisy Christophe, Mauduit Marc
Université de Rennes, Ecole Nationale Supérieure de Chimie de Rennes, CNRS, ISCR - UMR 6226, F-35000 Rennes, France.
Beilstein J Org Chem. 2020 Feb 17;16:212-232. doi: 10.3762/bjoc.16.24. eCollection 2020.
The copper-catalyzed enantioselective conjugate addition (ECA) of organometallic nucleophiles to electron-deficient alkenes (Michael acceptors) represents an efficient and attractive methodology for providing a wide range of relevant chiral molecules. In order to increase the attractiveness of this useful catalytic transformation, some Michael acceptors bearing challenging electron-deficient functions (i.e., aldehydes, thioesters, acylimidazoles, -acyloxazolidinones, -acylpyrrolidinones, amides, -acylpyrroles) were recently investigated. Remarkably, only a few chiral copper-based catalytic systems have successfully achieved the conjugate addition of different organometallic reagents to these challenging Michael acceptors, with excellent regio- and enantioselectivity. Furthermore, thanks to their easy derivatization, the resulting chiral conjugated products could be converted into various natural products. The aim of this tutorial review is to summarize recent advances accomplished in this stimulating field.
铜催化的有机金属亲核试剂对缺电子烯烃（迈克尔受体）的对映选择性共轭加成（ECA）是一种高效且有吸引力的方法，可用于制备多种相关的手性分子。为了提高这种有用的催化转化的吸引力，最近对一些带有具有挑战性的缺电子官能团（即醛、硫酯、酰基咪唑、酰基恶唑烷酮、酰基吡咯烷酮、酰胺、酰基吡咯）的迈克尔受体进行了研究。值得注意的是，只有少数基于手性铜的催化体系成功实现了不同有机金属试剂对这些具有挑战性的迈克尔受体的共轭加成，并具有出色的区域选择性和对映选择性。此外，由于其易于衍生化，所得的手性共轭产物可转化为各种天然产物。本教程综述的目的是总结在这个令人兴奋的领域中取得的最新进展。
