Tags

Type your tag names separated by a space and hit enter

Oxazaborolidinone-catalyzed enantioselective Friedel-Crafts alkylation of furans and indoles with alpha,beta-unsaturated ketones.
Org Lett. 2009 Nov 19; 11(22):5206-9.OL

Abstract

allo-Threonine-derived oxazaborolidinone (10 mol %) catalyzes the Friedel-Crafts alkylation of furans and indoles with simple acyclic alpha,beta-unsaturated ketones to give products with high yield and high enantioselectivity. The use of N,N-dimethylaniline (2.5-10 mol %) as an additive is essential for enantioselectivity.

Links

Publisher Full Text (DOI)

Authors+Show Affiliations

Adachi S
Department of Chemistry and Materials Technology, Kyoto Institute of Technology, Matsugasaki, Sakyo-ku, Kyoto, Japan 606-8585.
Tanaka F
No affiliation info available
Watanabe K
No affiliation info available
Harada T
No affiliation info available

MeSH

AlkylationBoranesCatalysisFuransHeterocyclic Compounds, 1-RingIndolesKetonesMolecular StructureStereoisomerism

Pub Type(s)

Journal Article

Language

eng

PubMed ID

19856925

Citation

Adachi, Shinya, et al. "Oxazaborolidinone-catalyzed Enantioselective Friedel-Crafts Alkylation of Furans and Indoles With Alpha,beta-unsaturated Ketones." Organic Letters, vol. 11, no. 22, 2009, pp. 5206-9.
Adachi S, Tanaka F, Watanabe K, et al. Oxazaborolidinone-catalyzed enantioselective Friedel-Crafts alkylation of furans and indoles with alpha,beta-unsaturated ketones. Org Lett. 2009;11(22):5206-9.
Adachi, S., Tanaka, F., Watanabe, K., & Harada, T. (2009). Oxazaborolidinone-catalyzed enantioselective Friedel-Crafts alkylation of furans and indoles with alpha,beta-unsaturated ketones. Organic Letters, 11(22), 5206-9. https://doi.org/10.1021/ol9021436
Adachi S, et al. Oxazaborolidinone-catalyzed Enantioselective Friedel-Crafts Alkylation of Furans and Indoles With Alpha,beta-unsaturated Ketones. Org Lett. 2009 Nov 19;11(22):5206-9. PubMed PMID: 19856925.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Oxazaborolidinone-catalyzed enantioselective Friedel-Crafts alkylation of furans and indoles with alpha,beta-unsaturated ketones. AU - Adachi,Shinya, AU - Tanaka,Fumi, AU - Watanabe,Kazuya, AU - Harada,Toshiro, PY - 2009/10/28/entrez PY - 2009/10/28/pubmed PY - 2010/1/15/medline SP - 5206 EP - 9 JF - Organic letters JO - Org Lett VL - 11 IS - 22 N2 - allo-Threonine-derived oxazaborolidinone (10 mol %) catalyzes the Friedel-Crafts alkylation of furans and indoles with simple acyclic alpha,beta-unsaturated ketones to give products with high yield and high enantioselectivity. The use of N,N-dimethylaniline (2.5-10 mol %) as an additive is essential for enantioselectivity. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/19856925/Oxazaborolidinone_catalyzed_enantioselective_Friedel_Crafts_alkylation_of_furans_and_indoles_with_alphabeta_unsaturated_ketones_ L2 - https://doi.org/10.1021/ol9021436 DB - PRIME DP - Unbound Medicine ER -