Literature DB >> 18986157

Tin-free enantioselective radical reactions using silanes.

Mukund P Sibi1, Yong-Hua Yang, Sunggi Lee.   

Abstract

Readily available hexyl silane is an excellent choice as a H-atom donor and a chain carrier in Lewis acid mediated enantioselective radical reactions. Conjugate radical additions to alpha,beta-unsaturated imides at room temperature proceed in good yields and excellent enantioselectivities.

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Year:  2008        PMID： 18986157      PMCID： PMC2765535          DOI： 10.1021/ol802154d

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


  18 in total

1.  Enantioselective Hydrogen Atom Transfer Reactions: Synthesis of N-Acyl-alpha-Amino Acid Esters This work was supported by the National Institutes of Health (NIH-GM-54656).

Authors:  Mukund P. Sibi; Yasutomi Asano; Justin B. Sausker
Journal:  Angew Chem Int Ed Engl       Date:  2001-04-01       Impact factor: 15.336

2.  Silylated Cyclohexadienes: New Alternatives to Tributyltin Hydride in Free Radical Chemistry We are grateful to Prof. Dr. Dieter Seebach for generous financial support and to Prof. Dr. Erick M. Carreira for helpful discussions during the preparation of the manuscript. We also thank the Swiss Science National Foundation (2100-055280.98/1) for funding our work.

Authors: 
Journal:  Angew Chem Int Ed Engl       Date:  2000-09-01       Impact factor: 15.336

3.  Hydrogen bond mediated enantioselectivity of radical reactions.

Authors:  Tobias Aechtner; Martina Dressel; Thorsten Bach
Journal:  Angew Chem Int Ed Engl       Date:  2004-11-05       Impact factor: 15.336

4.  Organocatalysis in radical chemistry. Enantioselective alpha-oxyamination of aldehydes.

Authors:  Mukund P Sibi; Masayuki Hasegawa
Journal:  J Am Chem Soc       Date:  2007-03-16       Impact factor: 15.419

5.  Enantioselective organocatalytic singly occupied molecular orbital activation: the enantioselective alpha-enolation of aldehydes.

Authors:  Hye-Young Jang; Jun-Bae Hong; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2007-05-12       Impact factor: 15.419

6.  (Me3Si)3SiH: twenty years after its discovery as a radical-based reducing agent.

Authors:  Chryssostomos Chatgilialoglu
Journal:  Chemistry       Date:  2008       Impact factor: 5.236

7.  Evolution of functional cyclohexadiene-based synthetic reagents: the importance of becoming aromatic.

Authors:  John C Walton; Armido Studer
Journal:  Acc Chem Res       Date:  2005-10       Impact factor: 22.384

8.  Silylated cyclohexadienes as new radical chain reducing reagents: preparative and mechanistic aspects.

Authors:  Armido Studer; Stephan Amrein; Florian Schleth; Tobias Schulte; John C Walton
Journal:  J Am Chem Soc       Date:  2003-05-14       Impact factor: 15.419

9.  Sustainable radical reduction through catalytic hydrogen atom transfer.

Authors:  Andreas Gansäuer; Chun-An Fan; Frederik Piestert
Journal:  J Am Chem Soc       Date:  2008-05-06       Impact factor: 15.419

10.  Thiophenol-mediated hydrogen atom abstraction: an efficient tin-free procedure for the preparation of cyclopentane derivatives.

Authors:  Florent Beaufils; Fabrice Dénès; Philippe Renaud
Journal:  Org Lett       Date:  2004-07-22       Impact factor: 6.005
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  2 in total

Review 1.  Recent applications of the (TMS)3SiH radical-based reagent.

Authors:  Chryssostomos Chatgilialoglu; Jacques Lalevée
Journal:  Molecules       Date:  2012-01-06       Impact factor: 4.411

2.  A chiral nickel DBFOX complex as a bifunctional catalyst for visible-light-promoted asymmetric photoredox reactions.

Authors:  Xiang Shen; Yanjun Li; Zhaorui Wen; Shi Cao; Xinyi Hou; Lei Gong
Journal:  Chem Sci       Date:  2018-04-27       Impact factor: 9.825
  2 in total

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