Catalytic Enantioselective Synthesis of Highly Functionalized Difluoromethylated Cyclopropanes. (18th September 2017)

• Record Type: Journal Article
• Authors: Bos, Maxence; Huang, Wei‐Sheng; Poisson, Thomas; Pannecoucke, Xavier; Charette, André B.; Jubault, Philippe
• Is Part Of: Angewandte Chemie. Volume 129:Number 43(2017)
• Page Start: 13504
• Page End: 13508
• Publication Date: 2017-09-18
• Subjects: Asymmetrische Katalyse -- Diazoverbindungen -- Fluor -- Rhodium -- Kleinringverbindungen; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201707375
• Languages: English
• ISSNs: 0044-8249

Abstract

Abstract: The first catalytic asymmetric synthesis of highly functionalized difluoromethylated cyclopropanes is described. The method, based on a rhodium‐catalyzed cyclopropanation of difluoromethylated olefins, gives access to a broad range of cyclopropanes bearing ester, ketone, or nitro functional groups. By using Rh2 (( S )‐BTPCP)4 as a catalyst, the corresponding products were obtained in high yields and high diastereo‐ and enantioselectivities (up 20:1 d.r. and 99 % ee ). This methodology allowed preparation of enantioenriched difluoromethylcyclopropanes for the first time.