Literature DB >> 17105282

Remarkably efficient enantioselective titanium(IV)-(R)-H8-BINOLate catalyst for arylations to aldehydes by triaryl(tetrahydrofuran)aluminum reagents.

Kuo-Hui Wu1, Han-Mou Gau.   

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.

Entities:  

Year:  2006        PMID: 17105282     DOI: 10.1021/ja062080y

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  5 in total

1.  Stereospecific cross-coupling of secondary organotrifluoroborates: potassium 1-(benzyloxy)alkyltrifluoroborates.

Authors:  Gary A Molander; Steven R Wisniewski
Journal:  J Am Chem Soc       Date:  2012-10-01       Impact factor: 15.419

2.  Triphen-yl(tetra-hydro-furan)-aluminium(III).

Authors:  Chi-Ren Chen; Han-Mou Gau
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-10-11

3.  Enantioselective synthesis of all-carbon quaternary stereogenic centers by catalytic asymmetric conjugate additions of alkyl and aryl aluminum reagents to five-, six-, and seven-membered-ring beta-substituted cyclic enones.

Authors:  Tricia L May; M Kevin Brown; Amir H Hoveyda
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

4.  Practical catalytic asymmetric synthesis of diaryl-, aryl heteroaryl-, and diheteroarylmethanols.

Authors:  Luca Salvi; Jeung Gon Kim; Patrick J Walsh
Journal:  J Am Chem Soc       Date:  2009-09-02       Impact factor: 15.419

5.  Efficient Approach to Carbinol Derivatives through Palladium-Catalyzed Base-Free Addition of Aryltriolborates to Aldehydes.

Authors:  Kun Hu; Pengqing Ye; Qianqian Zhen; Xinrong Yao; Tong Xu; Yinlin Shao; Jiuxi Chen
Journal:  Molecules       Date:  2017-09-20       Impact factor: 4.411

  5 in total

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