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Dynamic Kinetic Resolution of 2‐(Quinolin‐8‐yl)Benzaldehydes: Atroposelective Iridium‐Catalyzed Transfer Hydrogenative Allylation
Angewandte Chemie Pub Date : 2023-06-30 , DOI: 10.1002/ange.202306981
José A. Carmona 1 , Patricia Rodríguez‐Salamanca 1 , Rosario Fernández 2 , José M. Lassaletta 1 , Valentín Hornillos 1, 2
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AbstractAn atroposelective Ir‐catalyzed dynamic kinetic resolution (DKR) of 2‐(quinolin‐8‐yl)benzaldehydes/1‐naphthaldehydes by transfer hydrogenative coupling of allyl acetate is disclosed. The allylation reaction takes place with simultaneous installation of central and axial chirality, reaching high diastereoselectivities and excellent enantiomeric excesses when ortho‐cyclometalated iridium‐DM‐BINAP is used as the catalyst. The racemization of the substrates occurs through a designed transient Lewis acid‐base interaction between the quinoline nitrogen atom and the aldehyde carbonyl group.

中文翻译:

2-(喹啉-8-基)苯甲醛的动态动力学拆分:天体选择性铱催化转移氢化烯丙基化

摘要公开了通过乙酸烯丙酯的转移氢化偶联对 2-(喹啉-8-基)苯甲醛/1-萘醛进行间质选择性 Ir 催化动态动力学拆分 (DKR)。烯丙基化反应同时发生中心手性和轴向手性,达到高非对映选择性和优异的对映体过量正射使用-环金属化铱-DM-BINAP作为催化剂。底物的外消旋作用是通过喹啉氮原子和醛羰基之间设计的瞬时路易斯酸碱相互作用发生的。
更新日期:2023-06-30
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