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Remarkably efficient enantioselective titanium(IV)-(R)-H8-BINOLate catalyst for arylations to aldehydes by triaryl(tetrahydrofuran)aluminum reagents.
J Am Chem Soc. 2006 Nov 22; 128(46):14808-9.JA

Abstract

Novel asymmetric triarylaluminum AlAr3(THF) additions to aldehydes catalyzed by 10 mol % of the titanium(IV) complex of (R)-H8-BINOL ligand are reported. The catalytic system is extremely efficient with reactions completing within 10 min. The system applies to the most diversified aldehydes to date, and more than 20 aldehydes were examined to afford diarylmethanols having an electron-donating or an electron-withdrawing group at the 2-, 3-, or 4-position on the aryl moiety, linear or branched 1-aryl aliphatic alcohols, aryl furyl methanols, 1-aryl allylic alcohols, and, especially, 1-aryl propargylic alcohols in excellent enantioselectivities of >/=90% ee, except for the case of 1-naphthyl addition to benzaldehyde. Noteworthily, diarylmethanols in both R- and S-configurations can be obtained.

Authors+Show Affiliations

Department of Chemistry, National Chung-Hsing University, Taichung, Taiwan 402.No affiliation info available

Pub Type(s)

Journal Article

Language

eng

PubMed ID

17105282

Citation

Wu, Kuo-Hui, and Han-Mou Gau. "Remarkably Efficient Enantioselective titanium(IV)-(R)-H8-BINOLate Catalyst for Arylations to Aldehydes By Triaryl(tetrahydrofuran)aluminum Reagents." Journal of the American Chemical Society, vol. 128, no. 46, 2006, pp. 14808-9.
Wu KH, Gau HM. Remarkably efficient enantioselective titanium(IV)-(R)-H8-BINOLate catalyst for arylations to aldehydes by triaryl(tetrahydrofuran)aluminum reagents. J Am Chem Soc. 2006;128(46):14808-9.
Wu, K. H., & Gau, H. M. (2006). Remarkably efficient enantioselective titanium(IV)-(R)-H8-BINOLate catalyst for arylations to aldehydes by triaryl(tetrahydrofuran)aluminum reagents. Journal of the American Chemical Society, 128(46), 14808-9.
Wu KH, Gau HM. Remarkably Efficient Enantioselective titanium(IV)-(R)-H8-BINOLate Catalyst for Arylations to Aldehydes By Triaryl(tetrahydrofuran)aluminum Reagents. J Am Chem Soc. 2006 Nov 22;128(46):14808-9. PubMed PMID: 17105282.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Remarkably efficient enantioselective titanium(IV)-(R)-H8-BINOLate catalyst for arylations to aldehydes by triaryl(tetrahydrofuran)aluminum reagents. AU - Wu,Kuo-Hui, AU - Gau,Han-Mou, PY - 2006/11/16/pubmed PY - 2006/11/16/medline PY - 2006/11/16/entrez SP - 14808 EP - 9 JF - Journal of the American Chemical Society JO - J Am Chem Soc VL - 128 IS - 46 N2 - Novel asymmetric triarylaluminum AlAr3(THF) additions to aldehydes catalyzed by 10 mol % of the titanium(IV) complex of (R)-H8-BINOL ligand are reported. The catalytic system is extremely efficient with reactions completing within 10 min. The system applies to the most diversified aldehydes to date, and more than 20 aldehydes were examined to afford diarylmethanols having an electron-donating or an electron-withdrawing group at the 2-, 3-, or 4-position on the aryl moiety, linear or branched 1-aryl aliphatic alcohols, aryl furyl methanols, 1-aryl allylic alcohols, and, especially, 1-aryl propargylic alcohols in excellent enantioselectivities of >/=90% ee, except for the case of 1-naphthyl addition to benzaldehyde. Noteworthily, diarylmethanols in both R- and S-configurations can be obtained. SN - 0002-7863 UR - https://www.unboundmedicine.com/medline/citation/17105282/Remarkably_efficient_enantioselective_titanium_IV___R__H8_BINOLate_catalyst_for_arylations_to_aldehydes_by_triaryl_tetrahydrofuran_aluminum_reagents_ L2 - https://doi.org/10.1021/ja062080y DB - PRIME DP - Unbound Medicine ER -
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