Enantioselective Michael/Hemiketalization Cascade Reactions between Hydroxymaleimides and 2-Hydroxynitrostyrenes for the Construction of Chiral Chroman-Fused Pyrrolidinediones

Autor:	Dong-Hua Xie, Cheng Niu, Da-Ming Du
Jazyk:	angličtina
Rok vydání:	2022
Předmět:	organocatalysis asymmetric catalysis cascade reaction hydroxymaleimide chroman pyrrolidinedione Organic chemistry QD241-441
Zdroj:	Molecules, Vol 27, Iss 16, p 5081 (2022)
Druh dokumentu:	article
ISSN:	1420-3049
DOI:	10.3390/molecules27165081
Popis:	In this paper, the organocatalytic asymmetric Michael addition/hemiketalization cascade reactions between hydroxymaleimides and 2-hydroxynitrostyrenes were developed, which provided a new protocol for building a chiral ring-fused chroman skeleton. This squaramide-catalyzed cascade reaction provided chiral chroman-fused pyrrolidinediones with three contiguous stereocenters in good to high yields (up to 88%), with excellent diastereoselectivities (up to >20:1 dr) and enantioselectivities (up to 96% ee) at −16 °C. Moreover, a scale-up synthesis was also carried out, and a possible reaction mechanism was proposed.
Databáze:	Directory of Open Access Journals
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