Asymmetric Hydroacylation Involving Alkene Isomerization for the Construction of C3‐Chirogenic Center. (9th March 2021)

• Record Type: Journal Article
• Authors: Liu, Chong; Yuan, Jing; Zhang, Zhenfeng; Gridnev, Ilya D.; Zhang, Wanbin
• Is Part Of: Angewandte Chemie. Volume 133:Number 16(2021)
• Page Start: 9079
• Page End: 9084
• Publication Date: 2021-03-09
• Subjects: β-H elimination -- alkene isomerization -- cycloketones -- hydroacylation -- rhodacycle; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.202017190
• Languages: English
• ISSNs: 0044-8249

Abstract

Abstract: A new transformation pattern for enantioselective intramolecular hydroacylation has been developed involving an alkene isomerization strategy. Proceeding through a five‐membered rhodacycle intermediate, 3‐enals were converted to C3 ‐ or C3, C5 ‐chirogenic cyclopentanones with satisfactory yields, diastereoselectivities, and enantioselectivities. A catalytic cycle has been theoretically calculated and the origin of the stereoselection is rationally explained. Abstract : An enantioselective intramolecular hydroacylation of 3‐enals involving alkene isomerization was developed for the efficient construction of C3 ‐chirogenic cyclopentanones with satisfactory yields, diastereoselectivities, and enantioselectivities.