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Carbene-Catalyzed Activation of Formyl-phenylacetic Esters for Access to Chiral Dihydroisoquinolinones
Organic Letters ( IF 5.2 ) Pub Date : 2021-09-17 , DOI: 10.1021/acs.orglett.1c02676
Shuquan Wu 1 , Jun Xu 2, 3 , Rui Deng 1 , Hongling Wang 1 , Yonggui Robin Chi 1, 3 , Pengcheng Zheng 1
Affiliation  

A carbene-catalyzed reaction to synthesize chiral dihydroisoquinolinones via an o-quinodimethane (o-QDM) intermediate is disclosed. o-QDM reacts with cyclic sulfonic imines via annulation to afford highly enantioenriched dihydroisoquinolinone products. ESI-HRMS studies suggest a stepwise Mannich addition and acylation reaction pathway, and the pathways of the catalytic and uncatalyzed background reactions are evaluated via DFT calculations.

中文翻译:

卡宾催化活化甲酰苯乙酸酯以获得手性二氢异喹啉酮

公开了一种通过醌二甲烷 ( o- QDM) 中间体合成手性二氢异喹啉酮的卡宾催化反应。o -QDM 通过环化与环状磺酸亚胺反应,得到高度对映体富集的二氢异喹啉酮产品。ESI-HRMS 研究表明逐步曼尼希加成和酰化反应途径,催化和未催化背景反应的途径通过 DFT 计算进行评估。
更新日期:2021-10-01
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