Organocatalyst‐promoted Diastereoselective and Enantioselective Michael Addition/Hemiketalization Reaction between Hydroxymaleimide and Quinone. Issue 7 (10th June 2021)

• Record Type: Journal Article
• Authors: Xiang, Min; Li, Chen‐Yi; Zhang, Jian; Zou, Ying; Huang, Zhi‐Cheng; Li, Wen‐Sheng; Wang, Yi; Tian, Fang; Wang, Li‐Xin
• Is Part Of: Asian journal of organic chemistry. Volume 10:Issue 7(2021)
• Page Start: 1713
• Page End: 1717
• Publication Date: 2021-06-10
• Subjects: Domino reaction -- Enantioselective -- Hydroxymaleimides -- Organocatalysts -- Quinones; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; 547.005
• DOI: 10.1002/ajoc.202100291
• Languages: English
• ISSNs: 2193-5807

Abstract

Abstract: An organocatalyst promoted diastereoselective and enantioselective Michael addition/hemiketalization reaction between hydroxymaleimides and quinones has been demonstrated. The catalytic protocol allows for the efficient and mild synthesis of a broad range of new and versatile dihydrobenzofurans containing chiral hemiketal and succinimide frameworks from readily available starting materials in moderate to excellent yields (up to 95%) with good to excellent enantioselectivities (up to 95 : 5 er) and diastereoselectivities (all with at least 99 : 1 dr). Abstract : An organocatalyst‐promoted diastereoselective and enantioselective Michael addition/hemiketalization reaction between hydroxymaleimides and quinones has been demonstrated. The catalytic protocol allows for the efficient and mild synthesis of a broad range of new and versatile dihydrobenzofurans containing chiral hemiketal and succinimide frameworks from readily available starting materials in moderate to excellent yields (up to 95%) with good to excellent enantioselectivities (up to 95 : 5 er) and diastereoselectivities (all with at least 99 : 1 dr)