An asymmetric multicatalytic reaction sequence of 2-hydroxycinnamaldehydes and enolic 1,3-dicarbonyl compounds to construct bridged bicyclic acetals,Organic Chemistry Frontiers

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An asymmetric multicatalytic reaction sequence of 2-hydroxycinnamaldehydes and enolic 1,3-dicarbonyl compounds to construct bridged bicyclic acetals
Organic Chemistry Frontiers ( IF 4.6 ) Pub Date : 2019/12/02 , DOI: 10.1039/c9qo01272a
Xiao-Qian Zhang _{1,

2,

3,

4,

5} , Xue-Jiao Lv _{1,

2,

3,

4,

5} , Jun-Ping Pei _{1,

2,

3,

4,

5} , Rui Tan _{6,

7,

8,

9} , Yan-Kai Liu _{1,

2,

3,

4,

5}

Affiliation

An efficient asymmetric multicatalytic system involving iminium catalysis and anion-binding catalysis has been developed, which exhibited high catalytic activity in a one-pot, two-step reaction sequence of 2-hydroxycinnamaldehydes and enolic 1,3-dicarbonyl nucleophiles to construct an enantioenriched 2,8-dioxabicyclo[3.3.1]nonane scaffold. The inherent phenolic hydroxyl group of 2-hydroxycinnamaldehyde played an important role in the catalytic process, which potentially provided a phenoxide anion to combine with the thiourea moiety of a bifunctional tertiary amine-thiourea catalyst via anion binding, thus making the developed multicatalytic system more economic and different from the previously reported catalytic mode.

中文翻译：

2-羟基肉桂醛与烯键式1,3-二羰基化合物的不对称多催化反应序列，以构建桥联双环缩醛

已开发出一种有效的不对称多催化体系，该体系涉及亚胺基催化和阴离子结合催化，在2-羟基肉桂醛和烯醇式1,3-二羰基亲核试剂的一锅两步反应序列中表现出高催化活性，以构建对映体富集的2 ，8-二氧杂双环[3.3.1]壬烷骨架。2-羟基肉桂醛的固有酚羟基在催化过程中起着重要作用，它可能提供酚盐阴离子，通过阴离子键合与双功能叔胺-硫脲催化剂的硫脲部分结合，从而使开发的多催化体系更加经济与之前报道的催化模式不同。

更新日期：2020-02-13

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