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Acceleration of arylzinc formation and its enantioselective addition to aldehydes by microwave irradiation and aziridine-2-methanol catalysts.
J Org Chem. 2008 Apr 04; 73(7):2879-82.JO

Abstract

The formation and 2-amino alcohol catalyzed addition of arylzinc reagents from and with boronic acids, respectively, is drastically accelerated to a few minutes under microwave irradiation without loss of enantioselectivity (up to 98% ee). Of the amino acid derived catalysts tested, the conformationally restricted bulky substituted aziridine-2-methanols derived from serine show the best overall performance in the formation of diarylmethanols.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Braga AL
Universidade Federal de Santa Maria, Departamento de Química, 97105-900, Santa Maria RS, Brazil. albraga@quimica.ufsm.br
Paixão MW
No affiliation info available
Westermann B
No affiliation info available
Schneider PH
No affiliation info available
Wessjohann LA
No affiliation info available

MeSH

AlcoholsAldehydesAziridinesBoronic AcidsCatalysisLigandsMicrowavesMolecular StructureOrganometallic CompoundsStereoisomerismZinc

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

18315002

Citation

Braga, Antonio L., et al. "Acceleration of Arylzinc Formation and Its Enantioselective Addition to Aldehydes By Microwave Irradiation and Aziridine-2-methanol Catalysts." The Journal of Organic Chemistry, vol. 73, no. 7, 2008, pp. 2879-82.
Braga AL, Paixão MW, Westermann B, et al. Acceleration of arylzinc formation and its enantioselective addition to aldehydes by microwave irradiation and aziridine-2-methanol catalysts. J Org Chem. 2008;73(7):2879-82.
Braga, A. L., Paixão, M. W., Westermann, B., Schneider, P. H., & Wessjohann, L. A. (2008). Acceleration of arylzinc formation and its enantioselective addition to aldehydes by microwave irradiation and aziridine-2-methanol catalysts. The Journal of Organic Chemistry, 73(7), 2879-82. https://doi.org/10.1021/jo702413n
Braga AL, et al. Acceleration of Arylzinc Formation and Its Enantioselective Addition to Aldehydes By Microwave Irradiation and Aziridine-2-methanol Catalysts. J Org Chem. 2008 Apr 4;73(7):2879-82. PubMed PMID: 18315002.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Acceleration of arylzinc formation and its enantioselective addition to aldehydes by microwave irradiation and aziridine-2-methanol catalysts. AU - Braga,Antonio L, AU - Paixão,Marcio W, AU - Westermann,Bernhard, AU - Schneider,Paulo H, AU - Wessjohann,Ludger A, Y1 - 2008/03/04/ PY - 2008/3/5/pubmed PY - 2008/6/20/medline PY - 2008/3/5/entrez SP - 2879 EP - 82 JF - The Journal of organic chemistry JO - J Org Chem VL - 73 IS - 7 N2 - The formation and 2-amino alcohol catalyzed addition of arylzinc reagents from and with boronic acids, respectively, is drastically accelerated to a few minutes under microwave irradiation without loss of enantioselectivity (up to 98% ee). Of the amino acid derived catalysts tested, the conformationally restricted bulky substituted aziridine-2-methanols derived from serine show the best overall performance in the formation of diarylmethanols. SN - 0022-3263 UR - https://www.unboundmedicine.com/medline/citation/18315002/Acceleration_of_arylzinc_formation_and_its_enantioselective_addition_to_aldehydes_by_microwave_irradiation_and_aziridine_2_methanol_catalysts_ DB - PRIME DP - Unbound Medicine ER -