Organocatalytic enantioselective Diels–Alder reaction between hydroxymaleimides and in situ generated nitrosoalkenes for direct preparation of chiral hemiketals with 1,2-oxazine skeleton

文献情報

出版日 2021-08-30

DOI 10.1039/D1QO01022K

インパクトファクター 5.281

著者

Fang Tian, Wen-Juan Wan, Li-Xin Wang

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要旨

An organocatalyst promoted enantioselective inverse-electron-demand oxa-Diels–Alder (IEDDA) reaction between hydroxymaleimides and in situ generated nitrosoalkenes has been revealed, and a wide range of chiral hemiketals containing 5,6-dihydro-4H-1,2-oxazines and succinimide frameworks with two adjacent quaternary stereogenic centers have been effectively prepared for the first time with excellent results (up to 99% yield, up to 99 : 1 dr, up to >99% ee) even at a scale-up preparation under mild conditions.

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Organic Chemistry Frontiers

CiteScore: 7.8

自己引用率: 8.7%

年間論文数: 724

Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry

Organocatalytic enantioselective Diels–Alder reaction between hydroxymaleimides and in situ generated nitrosoalkenes for direct preparation of chiral hemiketals with 1,2-oxazine skeleton

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