Rhodium(III)‐Catalyzed Diastereoselective Synthesis of 1‐Aminoindanes via C−H Activation. Issue 22 (27th September 2017)

• Record Type: Journal Article
• Authors: Han, Sang Hoon; Mishra, Neeraj Kumar; Jeon, Mijin; Kim, Saegun; Kim, Hyung Sik; Jung, Seung‐Young; Jung, Young Hoon; Ku, Jin‐Mo; Kim, In Su
• Is Part Of: Advanced synthesis & catalysis. Volume 359:Issue 22(2017)
• Page Start: 3900
• Page End: 3904
• Publication Date: 2017-09-27
• Subjects: Aminoindanes -- C−H Activation -- Diastereoselectivity -- Imines -- Olefins -- Rhodium; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201701082
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: The rhodium(III)‐catalyzed cross‐coupling reaction between N ‐sulfonyl aldimines and various olefins such as maleimides, fumarates, maleates, α, β‐unsaturated ketones, acrylate and nitroalkenes is described. This transformation efficiently leads to the diastereoselective synthesis of pharmacologically privileged 1‐aminoindane derivatives via the C−H alkylation followed by subsequent intramolecular cyclization. Notably, single diastereomers in all cases were observed, and the relative stereochemistry of products was confirmed by the X‐ray crystallographic data. Abstract :