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北大黄湧课题组在Nature子刊报道有机催化领域取

来源:未知 编辑:admin 发布时间:2017-08-14
北大黄湧课题组在Nature子刊报道有机催化领域取得重要进展

化学生物学与生物技术学院黄湧课题组最近实现了首例利用氮杂卡宾的弱氢键作用来进行不对称催化。这项工作已经发表在《自然·通讯》杂志(Nature Communications)。该工作由北京大学深圳研究生院独立完成,化学基因组学博士生陈杰安为第一作者。

氮杂卡宾(NHC)是一类由相邻杂原子稳定的杂环类卡宾化合物。氮杂卡宾在二磷酸硫胺酶参与的多个生物合成过程中起到了重要的催化作用。

在这个生物催化机制的启发下,氮杂卡宾已经发展成为化学合成中最多才多艺的有机催化剂。此前,氮杂卡宾以非共价相互作用机制进行的不对称催化尚无报道。

原文摘要:

Asymmetric catalysis with N-heterocyclic carbenes as non-covalent chiral templates

Jiean Chen & Yong Huang

N-heterocyclic carbenes are a class of persistent carbenes stabilized by adjacent heteroatoms that are part of a heterocycle. They play a central role in multiple enzymatic biosynthetic reactions that involve thiamine diphosphate. Inspired by this biocatalysis machinery, N-heterocyclic carbenes have emerged as one of the most versatile classes of organocatalysts for organic reactions. However, the asymmetric synthesis of carbon–carbon bonds through a non-covalent interaction mechanism has not been previously established for chiral carbenes. Here, we report an N-heterocylic carbene-catalysed, highly enantioselective process that uses weak hydrogen bonds to relay asymmetric bias. We find that catalytic amounts of hexafluoroisopropanol are the critical proton shuttle that facilitates hydrogen transfer to provide high-reaction rates and high enantioselectivity. We demonstrate that a successful asymmetric reaction of this type can be accomplished through a rational design that balances the pKa values of the substrate, the carbene precursor and the product.

作者:北京大学 点击:

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