Literature DB >> 17385871

Intermolecular asymmetric reductive aldol reaction of ketones as acceptors promoted by chiral Rh(Phebox) catalyst.

Takushi Shiomi1, Hisao Nishiyama.   

Abstract

[reaction: see text] The conjugate reduction of cinnamates with hydrosilane and chiral Rh(Phebox-ip) catalyst in the presence of excess acetone is shown to provide the corresponding intermolecular reductive aldol product in extremely high enantioselectivity (up to 98%). Several cinnamates and crotonate substrates and several ketone acceptors were also examined.

Entities:  

Year:  2007        PMID： 17385871     DOI： 10.1021/ol070251d

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


  9 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

Review 3.  Metal-catalyzed reductive coupling of olefin-derived nucleophiles: Reinventing carbonyl addition.

Authors:  Khoa D Nguyen; Boyoung Y Park; Tom Luong; Hiroki Sato; Victoria J Garza; Michael J Krische
Journal:  Science       Date:  2016-10-21       Impact factor: 47.728

4.  Redox-triggered C-C coupling of diols and alkynes: synthesis of β,γ-unsaturated α-hydroxyketones and furans by ruthenium-catalyzed hydrohydroxyalkylation.

Authors:  Emma L McInturff; Khoa D Nguyen; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2014-03-17       Impact factor: 15.336

5.  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

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.  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

9.  Enantioselective Iridium-Catalyzed Reductive Coupling of Dienes with Oxetanones and N-Acyl-Azetidinones Mediated by 2-Propanol.

Authors:  Cole C Meyer; Zachary J Dubey; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2022-02-16       Impact factor: 15.336
  9 in total

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