Literature DB >> 16492037

Catalytic enantioselective Nozaki-Hiyama allylation reaction with tethered bis(8-quinolinolato) (TBOx) chromium complex.

Guoyao Xia1, Hisashi Yamamoto.   

Abstract

The utility of the new class of chiral ligand, tethered bis(8-quinolinol) (TBOxH), is further explored. Its chromium complex, TBOxCr(III)Cl, effectively catalyzes the Nozaki-Hiyama allylation reactions of various aldehydes at room temperature with high yield (up to 95%) and high enantioselectivity (up to 99% ee). The scope of the present method is shown to be wide, and this method represents an efficient access to chiral homoallylic alcohols.

Entities:  

Year:  2006        PMID: 16492037     DOI: 10.1021/ja058454p

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


  11 in total

1.  Polyol synthesis through hydrocarbon oxidation: de novo synthesis of L-galactose.

Authors:  Dustin J Covell; Nicolaas A Vermeulen; Nathan A Labenz; M Christina White
Journal:  Angew Chem Int Ed Engl       Date:  2006-12-11       Impact factor: 15.336

2.  Catalytic asymmetric Claisen rearrangement of enolphosphonates: construction of vicinal tertiary and all-carbon quaternary centers.

Authors:  Jiajing Tan; Cheol-Hong Cheon; Hisashi Yamamoto
Journal:  Angew Chem Int Ed Engl       Date:  2012-07-23       Impact factor: 15.336

3.  Iridium-catalyzed allylation of chiral β-stereogenic alcohols: bypassing discrete formation of epimerizable aldehydes.

Authors:  Daniel C Schmitt; Anne-Marie R Dechert-Schmitt; Michael J Krische
Journal:  Org Lett       Date:  2012-12-11       Impact factor: 6.005

Review 4.  Enantioselective iridium-catalyzed carbonyl allylation from the alcohol oxidation level via transfer hydrogenation: minimizing pre-activation for synthetic efficiency.

Authors:  Soo Bong Han; In Su Kim; Michael J Krische
Journal:  Chem Commun (Camb)       Date:  2009-10-16       Impact factor: 6.222

5.  Formation of C-C Bonds via Iridium-Catalyzed Hydrogenation and Transfer Hydrogenation.

Authors:  John F Bower; Michael J Krische
Journal:  Top Organomet Chem       Date:  2011-01-01       Impact factor: 1.311

6.  Catalytic enantioselective Grignard Nozaki-Hiyama methallylation from the alcohol oxidation level: chloride compensates for π-complex instability.

Authors:  Abbas Hassan; Ian A Townsend; Michael J Krische
Journal:  Chem Commun (Camb)       Date:  2011-08-10       Impact factor: 6.222

7.  Diastereo- and enantioselective ruthenium-catalyzed hydrohydroxyalkylation of 2-silyl-butadienes: carbonyl syn-crotylation from the alcohol oxidation level.

Authors:  Jason R Zbieg; Joseph Moran; Michael J Krische
Journal:  J Am Chem Soc       Date:  2011-06-16       Impact factor: 15.419

8.  anti-Diastereo- and enantioselective carbonyl crotylation from the alcohol or aldehyde oxidation level employing a cyclometallated iridium catalyst: alpha-methyl allyl acetate as a surrogate to preformed crotylmetal reagents.

Authors:  In Su Kim; Soo Bong Han; Michael J Krische
Journal:  J Am Chem Soc       Date:  2009-02-25       Impact factor: 15.419

9.  Chromium(II)-catalyzed enantioselective arylation of ketones.

Authors:  Gang Wang; Shutao Sun; Ying Mao; Zhiyu Xie; Lei Liu
Journal:  Beilstein J Org Chem       Date:  2016-12-19       Impact factor: 2.883

Review 10.  Allenes and Dienes as Chiral Allylmetal Pronucleophiles in Catalytic Enantioselective C=X Addition: Historical Perspective and State-of-The-Art Survey.

Authors:  Ming Xiang; Dana E Pfaffinger; Michael J Krische
Journal:  Chemistry       Date:  2021-07-29       Impact factor: 5.020

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