Literature DB >> 18847266

CuH-catalyzed enantioselective intramolecular reductive aldol reactions generating three new contiguous asymmetric stereocenters.

Bruce H Lipshutz1, Benjamin Amorelli, John B Unger.   

Abstract

Treatment of beta,beta-disubstituted-alpha,beta-unsaturated ketones bearing a ketone residue with in situ generated, catalytic CuH ligated by a nonracemic ligand leads to three newly created adjacent chiral centers. Excellent de's and ee's are obtained for several examples studied.

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Year:  2008        PMID： 18847266     DOI： 10.1021/ja8045475

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


  8 in total

1.  Enantioselective Synthesis of β-Amino Acid Derivatives Enabled by Ligand-Controlled Reversal of Hydrocupration Regiochemistry.

Authors:  Sheng Guo; Jiaqi Zhu; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2020-09-11       Impact factor: 15.336

2.  Generation of stereochemically defined tetrasubstituted enolborinates by 1,4-hydroboration of α,β-unsaturated morpholine carboxamides with (diisopinocampheyl)borane.

Authors:  Christophe Allais; Andy S Tsai; Philippe Nuhant; William R Roush
Journal:  Angew Chem Int Ed Engl       Date:  2013-10-15       Impact factor: 15.336

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.  Copper-catalyzed asymmetric addition of olefin-derived nucleophiles to ketones.

Authors:  Yang Yang; Ian B Perry; Gang Lu; Peng Liu; Stephen L Buchwald
Journal:  Science       Date:  2016-06-09       Impact factor: 47.728

7.  Magnesium-catalyzed asymmetric direct aldol addition of ethyl diazoacetate to aromatic, aliphatic, and alpha,beta-unsaturated aldehydes.

Authors:  Barry M Trost; Sushant Malhotra; Benjamin A Fried
Journal:  J Am Chem Soc       Date:  2009-02-11       Impact factor: 15.419

8.  Enantioselective CuH-Catalyzed Reductive Coupling of Aryl Alkenes and Activated Carboxylic Acids.

Authors:  Jeffrey S Bandar; Erhad Ascic; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2016-04-29       Impact factor: 15.419
  8 in total

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