Literature DB >> 17031933

Pyrones to pyrans: enantioselective radical additions to acyloxy pyrones.

Mukund P Sibi1, Jake Zimmerman.   

Abstract

This paper describes a highly site-, diastereo-, and enantioselective intermolecular radical addition/hydrogen atom transfer to hydroxypyrone pyromeconic and kojic acids. The methodology can be extended to the formation of chiral quaternary centers. The products obtained are densely functionalized pyran moieties. The products contain structural features amenable for the introduction of additional substituents.

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Year:  2006        PMID： 17031933      PMCID： PMC2531155          DOI： 10.1021/ja0648108

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


  15 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.  Enantioselective radical processes.

Authors:  Mukund P Sibi; Shankar Manyem; Jake Zimmerman
Journal:  Chem Rev       Date:  2003-08       Impact factor: 60.622

3.  Enantioselective H-atom transfer reactions: a new methodology for the synthesis of beta2-amino acids.

Authors:  Mukund P Sibi; Kalyani Patil
Journal:  Angew Chem Int Ed Engl       Date:  2004-02-27       Impact factor: 15.336

4.  Enantioselective H-atom transfer reaction: a strategy to synthesize formaldehyde aldol products.

Authors:  Mukund P Sibi; Kalyani Patil
Journal:  Org Lett       Date:  2005-04-14       Impact factor: 6.005

5.  The role of the achiral template in enantioselective transformations. Radical conjugate additions to alpha-methacrylates followed by hydrogen atom transfer.

Authors:  Mukund P Sibi; Justin B Sausker
Journal:  J Am Chem Soc       Date:  2002-02-13       Impact factor: 15.419

6.  Highly enantioselective conjugate additions to alpha,beta-unsaturated ketones catalyzed by a (salen)Al complex.

Authors:  Mark S Taylor; David N Zalatan; Andreas M Lerchner; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2005-02-02       Impact factor: 15.419

7.  Axially chiral biaryl diols catalyze highly enantioselective hetero-Diels-Alder reactions through hydrogen bonding.

Authors:  Aditya K Unni; Norito Takenaka; Hisashi Yamamoto; Viresh H Rawal
Journal:  J Am Chem Soc       Date:  2005-02-09       Impact factor: 15.419

8.  Unified synthesis of quinone sesquiterpenes based on a radical decarboxylation and quinone addition reaction.

Authors:  Taotao Ling; Erwan Poupon; Erik J Rueden; Sun H Kim; Emmanuel A Theodorakis
Journal:  J Am Chem Soc       Date:  2002-10-16       Impact factor: 15.419

9.  Broadly effective enantioselective Diels-Alder reactions of 1-amino-substituted-1,3-butadienes.

Authors:  Yong Huang; Tetsuo Iwama; Viresh H Rawal
Journal:  Org Lett       Date:  2002-04-04       Impact factor: 6.005

10.  Evolution of dithiane-based strategies for the construction of architecturally complex natural products.

Authors:  Amos B Smith; Christopher M Adams
Journal:  Acc Chem Res       Date:  2004-06       Impact factor: 22.384
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  2 in total

1.  Enantioselective conjugate additions of α-amino radicals via cooperative photoredox and Lewis acid catalysis.

Authors:  Laura Ruiz Espelt; Iain S McPherson; Eric M Wiensch; Tehshik P Yoon
Journal:  J Am Chem Soc       Date:  2015-02-16       Impact factor: 15.419

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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