Issue 63, 2021

Asymmetric [4 + 2] cycloaddition synthesis of 4H-chromene derivatives facilitated by group-assisted-purification (GAP) chemistry

Abstract

In this work, we present a strategy for the preparation of functionalized 4H-chromene derivatives via a Cs2CO3-catalyzed [4 + 2] cycloaddition of enantiopure chiral salicyl N-phosphonyl imines with allenoates. Fifteen examples were achieved in excellent yields and diastereoselectivity. The products were purified simply by washing the crude mixture with hexanes following the Group-Assisted Purification (GAP) chemistry/technology to bypass traditional separation methods. The absolute configuration was unambiguously determined by X-ray structure analysis.

Graphical abstract: Asymmetric [4 + 2] cycloaddition synthesis of 4H-chromene derivatives facilitated by group-assisted-purification (GAP) chemistry

Supplementary files

Article information

Article type
Paper
Submitted
15 noy 2021
Accepted
06 dek 2021
First published
14 dek 2021
This article is Open Access
Creative Commons BY license

RSC Adv., 2021,11, 39790-39796

Asymmetric [4 + 2] cycloaddition synthesis of 4H-chromene derivatives facilitated by group-assisted-purification (GAP) chemistry

H. Rouh, Y. Tang, S. Zhang, A. I. M. Ali, K. Surowiec, D. Unruh and G. Li, RSC Adv., 2021, 11, 39790 DOI: 10.1039/D1RA08323F

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