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Chiral tertiary 2-furyl alcohols: diversified key intermediates to bioactive compounds. Their enantioselective synthesis via (2-furyl)aluminium addition to ketones catalyzed by a titanium catalyst of (S)-BINOL.
Chem Commun (Camb). 2008 May 28CC

Abstract

Novel asymmetric 2-furyl additions of (2-furyl)AlEt(2)(THF) to aromatic ketones and one alpha,beta-unsaturated ketone catalyzed by a titanium catalyst of 10-20 mol% (S)-BINOL are reported to furnish tertiary furyl alcohols in good to excellent enantioselectivities of 87-93% ee.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Wu KH
Department of Chemistry, National Chung Hsing University, Taichung 402, Taiwan, Republic of China.
Chuang DW
No affiliation info available
Chen CA
No affiliation info available
Gau HM
No affiliation info available

MeSH

AlcoholsAluminumCatalysisFuransKetonesNaphtholsOrganometallic CompoundsStereoisomerismTitanium

Pub Type(s)

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

Language

eng

PubMed ID

18473064

Citation

Wu, Kuo-Hui, et al. "Chiral Tertiary 2-furyl Alcohols: Diversified Key Intermediates to Bioactive Compounds. Their Enantioselective Synthesis Via (2-furyl)aluminium Addition to Ketones Catalyzed By a Titanium Catalyst of (S)-BINOL." Chemical Communications (Cambridge, England), 2008, pp. 2343-5.
Wu KH, Chuang DW, Chen CA, et al. Chiral tertiary 2-furyl alcohols: diversified key intermediates to bioactive compounds. Their enantioselective synthesis via (2-furyl)aluminium addition to ketones catalyzed by a titanium catalyst of (S)-BINOL. Chem Commun (Camb). 2008.
Wu, K. H., Chuang, D. W., Chen, C. A., & Gau, H. M. (2008). Chiral tertiary 2-furyl alcohols: diversified key intermediates to bioactive compounds. Their enantioselective synthesis via (2-furyl)aluminium addition to ketones catalyzed by a titanium catalyst of (S)-BINOL. Chemical Communications (Cambridge, England), (20), 2343-5. https://doi.org/10.1039/b802441c
Wu KH, et al. Chiral Tertiary 2-furyl Alcohols: Diversified Key Intermediates to Bioactive Compounds. Their Enantioselective Synthesis Via (2-furyl)aluminium Addition to Ketones Catalyzed By a Titanium Catalyst of (S)-BINOL. Chem Commun (Camb). 2008 May 28;(20)2343-5. PubMed PMID: 18473064.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Chiral tertiary 2-furyl alcohols: diversified key intermediates to bioactive compounds. Their enantioselective synthesis via (2-furyl)aluminium addition to ketones catalyzed by a titanium catalyst of (S)-BINOL. AU - Wu,Kuo-Hui, AU - Chuang,Da-Wei, AU - Chen,Chien-An, AU - Gau,Han-Mou, Y1 - 2008/04/17/ PY - 2008/5/14/pubmed PY - 2008/6/27/medline PY - 2008/5/14/entrez SP - 2343 EP - 5 JF - Chemical communications (Cambridge, England) JO - Chem Commun (Camb) IS - 20 N2 - Novel asymmetric 2-furyl additions of (2-furyl)AlEt(2)(THF) to aromatic ketones and one alpha,beta-unsaturated ketone catalyzed by a titanium catalyst of 10-20 mol% (S)-BINOL are reported to furnish tertiary furyl alcohols in good to excellent enantioselectivities of 87-93% ee. SN - 1359-7345 UR - https://www.unboundmedicine.com/medline/citation/18473064/Chiral_tertiary_2_furyl_alcohols:_diversified_key_intermediates_to_bioactive_compounds__Their_enantioselective_synthesis_via__2_furyl_aluminium_addition_to_ketones_catalyzed_by_a_titanium_catalyst_of__S__BINOL_ DB - PRIME DP - Unbound Medicine ER -