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Palladium‐Catalyzed Enantioselective Addition of Chiral Metal Enolates to In Situ Generated ortho‐Quinone Methides
Angewandte Chemie International Edition ( IF 16.6 ) Pub Date : 2018-10-18 , DOI: 10.1002/anie.201809692
Fabian Göricke 1 , Christoph Schneider 1
Affiliation  

We describe herein a conceptually novel, cooperative Brønsted acid/base catalyzed process for the conjugate addition of cyclic β‐keto esters to ortho‐quinone methides both generated in situ. Upon hemiacetalization, densely functionalized chiral chromans with two adjacent quaternary and additionally a tertiary stereogenic center were obtained with very good diastereoselectivity (up to >95:5 d.r.) and typically excellent enantioselectivity (up to >99 % ee). The striking feature and key to success is the dual catalytic activation of both nucleophile and electrophile in two separate cycles with a single chiral catalyst.

中文翻译:

手性金属烯醇化物的钯催化对映选择性加成到原位生成的邻醌醌甲基化物中

我们在这里描述了一种概念上新颖的,协同的布朗斯台德酸/碱催化方法,用于将环β-酮酸酯共轭加成到原位生成的醌甲基化物中。半缩醛化后,获得具有两个相邻的季铵盐和一个三级立体异构中心的致密官能化手性二价铬,具有非常好的非对映选择性(高达> 95:5 dr)和典型的出色的对映选择性(高达> 99%ee)。显着的特点和成功的关键是亲核试剂和亲电试剂在两个单独的循环中用单一手性催化剂进行双重催化活化。
更新日期:2018-10-18
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