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Enantioselective Addition of Alkynyl Esters and Ethers to Aldehydes Catalyzed by a Cyclopropyl Amino Alcohol Based Zinc Catalyst
Synlett ( IF 2 ) Pub Date : 2019-12-03 , DOI: 10.1055/s-0039-1690264
Yun Zhou 1 , Lifeng Wang 1 , Shuoning Li 1 , Sijie Ma 1 , Patrick J. Walsh 2 , Qinghua Bian 1 , Fengqi Li 3 , Min Wang 1 , Jiangchun Zhong 1
Affiliation  

A novel and highly enantioselective synthesis of hydroxyalkynyl esters and ethers through the asymmetric addition of alkynyl esters or ethers to aldehydes promoted by a cyclopropyl amino alcohol based zinc catalyst has been developed. The method afforded a library of new enantioenriched hydroxyalkynol esters and ethers (up to 93% yield; 95% ee), and it was compatible with a broad range of functional groups. Moreover, it could be used in the synthesis of carbon-chain-elongated enantioenriched hydroxyalkynol esters and (2R,5R)-musclide-A1, a cardiotonic potentiating principle from musk.

中文翻译:

环丙基氨基醇基锌催化剂催化炔基酯和醚对醛的对映选择性加成

通过在环丙氨基醇基锌催化剂的促进下将炔基酯或醚不对称加成到醛上,开发了一种新型的、高度对映选择性的羟基炔基酯和醚的合成方法。该方法提供了一个新的对映体富集的羟基炔醇酯和醚的库(产率高达 93%;95% ee),并且它与广泛的官能团兼容。此外,它还可以用于合成碳链延长的对映体富集的羟基炔醇酯和 (2R,5R)-musclide-A1,这是一种来自麝香的强心剂。
更新日期:2019-12-03
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