Fiaud’s Acid: A Brønsted Acid Catalyst for Enantioselective Friedel− Crafts Alkylation of Indoles with 2‑Alkene-1,4-diones
IR@IICB: CSIR-Indian Institute of Chemical Biology, Kolkata
View Archive Info| Field | Value | |
| 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/ |
|