Copper-Catalyzed Enantioselective Coupling between Allylboronates and Phosphates with a Phenol-Carbene Chiral Ligand: Asymmetric Synthesis of Chiral Branched 1,5-Dienes
Copper-Catalyzed Enantioselective Coupling between Allylboronates and Phosphates with a Phenol-Carbene Chiral Ligand: Asymmetric Synthesis of Chiral Branched 1,5-Dienes
复制标题
铜催化烯丙基硼酸酯和磷酸酯与苯酚卡宾手性配体之间的对映选择性偶联：手性支化 1,5-二烯的不对称合成
DOI：
10.1055/s-0036-1591548
复制
发表时间：
2018
期刊：
影响因子：
--
通讯作者：
M.
中科院分区：
文献类型：
--
作者：
Yasuda;Y.; Ohmiya;H.; Sawamura;M.
本文介绍了一种新的手性n -杂环羰基（NHC）配体在铜催化的硼烯丙酸酯和(Z)-烯丙基磷酸之间的对映选择性偶联反应。铜催化产生具有三级立体中心的富集对映体的手性1,5-二烯。与各种官能团的相容性以及使用地球上资源丰富且毒性相对较低的铜作为金属是该协议的吸引人的特点。证明了手性苯酚- nhc配体在铜与有机硼化合物的对映选择性催化中的应用，并讨论了对映辨别模型。
Details of the Cu-catalyzed enantioselective allyl–allyl coupling reaction between allylboronates and (Z)-allylic phosphates using a new chiralN-heterocyclic carbene (NHC) ligand containing a phenolic hydroxy group are presented. The copper catalysis delivers enantioenriched chiral 1,5-dienes with a tertiary stereogenic center. Compatibility with various functional groups and the use of earth-abundant and relatively low-toxicity copper as a metal are attractive features of this protocol. The utility of the chiral phenol–NHC ligand for enantioselective copper catalysis with organoboron compounds is demonstrated and enantiodiscrimination models are discussed.