Literature DB >> 15070315

Asymmetric 1,4-reductions of hindered beta-substituted cycloalkenones using catalytic SEGPHOS-ligated CuH.

Bruce H Lipshutz1, Jeff M Servesko, Tue B Petersen, Patrick P Papa, Andrew A Lover.   

Abstract

The reagent combination of catalytic amounts of copper hydride ligated by a nonracemic SEGPHOS ligand leads in situ to an extremely reactive species capable of effecting asymmetric hydrosilylations of conjugated cyclic enones in very high ees. An unprecedented substrate-to-ligand ratio as high as 275 000:1 for this transformation has been documented. [reaction: see text]

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Year:  2004        PMID: 15070315     DOI: 10.1021/ol0400185

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


  7 in total

1.  Application of a C2-symmetric copper carbenoid in the enantioselective hydrosilylation of dialkyl and aryl-alkyl ketones.

Authors:  Abigail Albright; Robert E Gawley
Journal:  J Am Chem Soc       Date:  2011-11-16       Impact factor: 15.419

2.  CuH-Catalyzed Asymmetric Reduction of α,β-Unsaturated Carboxylic Acids to β-Chiral Aldehydes.

Authors:  Yujing Zhou; Jeffrey S Bandar; Richard Y Liu; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2018-01-04       Impact factor: 15.419

3.  Mechanistic Insight Facilitates Discovery of a Mild and Efficient Copper-Catalyzed Dehydration of Primary Amides to Nitriles Using Hydrosilanes.

Authors:  Richard Y Liu; Minwoo Bae; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2018-01-29       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.  Asymmetric synthesis of chiral β-alkynyl carbonyl and sulfonyl derivatives via sequential palladium and copper catalysis.

Authors:  Barry M Trost; James T Masters; Benjamin R Taft; Jean-Philip Lumb
Journal:  Chem Sci       Date:  2016-06-10       Impact factor: 9.825

6.  Silicon Industry Waste Polymethylhydrosiloxane-Mediated Benzotriazole Ring Cleavage: A Practical and Green Synthesis of Diverse Benzothiazoles.

Authors:  Mangal S Yadav; Anoop S Singh; Anand K Agrahari; Nidhi Mishra; Vinod K Tiwari
Journal:  ACS Omega       Date:  2019-04-11

7.  Enantioselective conjugate hydrosilylation of α,β-unsaturated ketones.

Authors:  Huan Yang; Guanglin Weng; Dongmei Fang; Changjiang Peng; Yuanyuan Zhang; Xiaomei Zhang; Zhouyu Wang
Journal:  RSC Adv       Date:  2019-04-12       Impact factor: 4.036

  7 in total

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