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Enantioselective Friedel-Crafts Alkylation of Furans and Indoles with Simple α,β-Unsaturated Ketones Catalyzed by Oxazaborolidinone
| Content Provider | Scilit |
|---|---|
| Author | Harada, Toshiro Adachi, Shinya Tanaka, Fumi Watanabe, Kazuya Watada, Atsushi |
| Copyright Year | 2010 |
| Description | allo-Threonine-derived oxazaborolidinone (OXB) catalyzes the Friedel-Crafts alkylation of furans and indoles with simple acyclic α,β-unsaturated ketones to give the products in high yields and with high enantioselectivities. With 5-10 mol% of the OXB catalyst, enantioselectivities of up to 94% ee could be achieved for a variety of substrates. The use of N,N-dimethylaniline (2.5-10 mol%) as an additive is found to be essential for enantioselectivity. The effects of the additive are discussed in terms of the retardation of a proton-catalyzed racemic pathway, which deteriorates the enantioselectivity of the Friedel-Crafts reactions. |
| Related Links | http://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-0029-1218821.pdf |
| Ending Page | 2669 |
| Page Count | 18 |
| Starting Page | 2652 |
| ISSN | 00397881 |
| e-ISSN | 1437210X |
| DOI | 10.1055/s-0029-1218821 |
| Journal | Synthesis |
| Issue Number | 15 |
| Volume Number | 2010 |
| Language | English |
| Publisher | Georg Thieme Verlag KG |
| Publisher Date | 2010-06-18 |
| Access Restriction | Open |
| Subject Keyword | Journal: Synthesis Organic Chemistry Asymmetric Catalysis Friedel-crafts Reaction |
| Content Type | Text |
| Resource Type | Article |
| Subject | Organic Chemistry Catalysis |
