Literature DB >> 17107096

Reductive aldol coupling of divinyl ketones via rhodium-catalyzed hydrogenation: syn-diastereoselective construction of beta-hydroxyenones.

Soo Bong Han1, Michael J Krische.   

Abstract

Catalytic hydrogenation of divinyl ketones 1a and 1e in the presence of diverse aldehydes 2a-e at ambient temperature and pressure using cationic rhodium catalysts ligated by tri-2-furyl phosphine enables formation of aldol products 3a-e and 5a-e, respectively, with high levels of syn diastereoselection. Through an assay of counterions (Rh(COD)2X), Rh(COD)2SbF6 is identified as the optimum precatalyst for reductive aldol couplings of this type. For para-substituted styryl vinyl ketones 1b-e, a progressive increase in isolated yield is observed for electron-releasing para substituents. [reaction: see text].

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Year:  2006        PMID： 17107096     DOI： 10.1021/ol0624023

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  11 in total

1.  Formation of C-C Bonds via Catalytic Hydrogenation and Transfer Hydrogenation: Vinylation, Allylation, and Enolate Addition of Carbonyl Compounds and Imines.

Authors:  Ryan L Patman; John F Bower; In Su Kim; Michael J Krische
Journal:  Aldrichimica Acta       Date:  2008       Impact factor: 3.667

2.  Diastereo- and Enantioselective Reductive Aldol Addition of Vinyl Ketones via Catalytic Hydrogenation.

Authors:  Soo Bong Han; Abbas Hassan; Michael J Krische
Journal:  Synthesis (Stuttg)       Date:  2008-09-01       Impact factor: 3.157

3.  ESI-MS, DFT, and synthetic studies on the H(2)-mediated coupling of acetylene: insertion of C=X bonds into rhodacyclopentadienes and Brønsted acid cocatalyzed hydrogenolysis of organorhodium intermediates.

Authors:  Vanessa M Williams; Jong Rock Kong; Byoung Joon Ko; Yogita Mantri; Jennifer S Brodbelt; Mu-Hyun Baik; Michael J Krische
Journal:  J Am Chem Soc       Date:  2009-11-11       Impact factor: 15.419

4.  Catalytic Reductive Aldol and Mannich Reactions of Enone, Acrylate, and Vinyl Heteroaromatic Pronucleophiles.

Authors:  Cole C Meyer; Eliezer Ortiz; Michael J Krische
Journal:  Chem Rev       Date:  2020-03-19       Impact factor: 60.622

5.  anti-Aminoallylation of aldehydes via ruthenium-catalyzed transfer hydrogenative coupling of sulfonamido allenes: 1,2-aminoalcohols.

Authors:  Eduardas Skucas; Jason R Zbieg; Michael J Krische
Journal:  J Am Chem Soc       Date:  2009-04-15       Impact factor: 15.419

6.  Diisopinocampheylborane-mediated reductive aldol reactions: highly enantio- and diastereoselective synthesis of syn aldols from N-acryloylmorpholine.

Authors:  Philippe Nuhant; Christophe Allais; William R Roush
Journal:  Angew Chem Int Ed Engl       Date:  2013-07-01       Impact factor: 15.336

7.  L-selectride-mediated highly diastereoselective asymmetric reductive aldol reaction: access to an important subunit for bioactive molecules.

Authors:  Arun K Ghosh; Jorden Kass; David D Anderson; Xiaoming Xu; Christine Marian
Journal:  Org Lett       Date:  2008-10-03       Impact factor: 6.005

8.  Branch-selective reductive coupling of 2-vinyl pyridines and imines via rhodium catalyzed C-C bond forming hydrogenation.

Authors:  Venukrishnan Komanduri; Christopher D Grant; Michael J Krische
Journal:  J Am Chem Soc       Date:  2008-08-29       Impact factor: 15.419

9.  Diastereo- and enantioselective hydrogenative aldol coupling of vinyl ketones: design of effective monodentate TADDOL-like phosphonite ligands.

Authors:  Cisco Bee; Soo Bong Han; Abbas Hassan; Hiroki Iida; Michael J Krische
Journal:  J Am Chem Soc       Date:  2008-02-12       Impact factor: 15.419

10.  From Hydrogenation to Transfer Hydrogenation to Hydrogen Auto-Transfer in Enantioselective Metal-Catalyzed Carbonyl Reductive Coupling: Past, Present, and Future.

Authors:  Catherine Gazolla Santana; Michael J Krische
Journal:  ACS Catal       Date:  2021-04-22       Impact factor: 13.084
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