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Fiaud’s Acid: A Brønsted Acid Catalyst for Enantioselective Friedel− Crafts Alkylation of Indoles with 2‑Alkene-1,4-diones

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Title Fiaud’s Acid: A Brønsted Acid Catalyst for Enantioselective Friedel− Crafts Alkylation of Indoles with 2‑Alkene-1,4-diones
 
Creator Chatterjee, Sourav
Hintermann, Lukas
Mandal, Madhumita
Achari, Anushree
Gupta, Sreya
Jaisankar, Parasuraman
 
Subject Chemistry
 
Description Fiaud’s acid (trans-1-hydroxy-2,5-diphenylphospholane
1-oxide), a phospholane-based phosphinic acid, is
introduced as an efficient chiral Brønsted acid catalyst that mediates the asymmetric Friedel−Crafts alkylation of indoles with 2-butene-1,4-diones. With a catalyst loading of 10 mol %,the reaction proceeded smoothly to afford 2-(indol-3-yl)butane-1,4-diones in high yield (up to 82%) and high enantioselectivity(up to 91% ee, one such product showed enhanced ee of 98% after ecrystallization). The reaction conditions are sufficiently mild to tolerate sensitive functionality at room temperature and are therefore suitable for the synthesis of complex targets.
 
Publisher American Chemical Society
 
Date 2017
 
Type Article
PeerReviewed
 
Format application/pdf
 
Identifier http://www.eprints.iicb.res.in/2718/1/Organic_Letters.pdf
Chatterjee, Sourav and Hintermann, Lukas and Mandal, Madhumita and Achari, Anushree and Gupta, Sreya and Jaisankar, Parasuraman (2017) Fiaud’s Acid: A Brønsted Acid Catalyst for Enantioselective Friedel− Crafts Alkylation of Indoles with 2‑Alkene-1,4-diones. Organic Letters, 19. pp. 3426-3429.
 
Relation http://dx.doi.org/10.1021/acs.orglett.7b01383
http://www.eprints.iicb.res.in/2718/