Literature DB >> 16146393

Cu(I)-catalyzed reductive aldol cyclizations: diastereo- and enantioselective synthesis of beta-hydroxylactones.

Hon Wai Lam1, Pekka M Joensuu.   

Abstract

[reaction: see text] Copper bisphosphine complexes catalyze the intramolecular reductive aldol reaction of alpha,beta-unsaturated esters with ketones, affording five- and six-membered beta-hydroxylactones in high stereoselectivities. Utilization of chiral nonracemic bisphosphines render the cyclizations enantioselective.

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Year:  2005        PMID： 16146393     DOI： 10.1021/ol051649h

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

3.  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

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.  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

6.  Optimizing P,N-bidentate ligands for oxidative gold catalysis: efficient intermolecular trapping of α-oxo gold carbenes by carboxylic acids.

Authors:  Kegong Ji; Yulong Zhao; Liming Zhang
Journal:  Angew Chem Int Ed Engl       Date:  2013-05-02       Impact factor: 15.336

7.  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

8.  Direct catalytic enantio- and diastereoselective ketone aldol reactions of isocyanoacetates.

Authors:  Raquel de la Campa; Irene Ortín; Darren J Dixon
Journal:  Angew Chem Int Ed Engl       Date:  2015-03-03       Impact factor: 15.336

9.  Biosynthesis of dendroketose from different carbon sources using in vitro and in vivo metabolic engineering strategies.

Authors:  Jiangang Yang; Yueming Zhu; Ge Qu; Yan Zeng; Chaoyu Tian; Caixia Dong; Yan Men; Longhai Dai; Zhoutong Sun; Yuanxia Sun; Yanhe Ma
Journal:  Biotechnol Biofuels       Date:  2018-10-25       Impact factor: 6.040
  9 in total

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