Literature DB >> 19715274

Corey-Chaykovsky epoxidation of twisted amides: synthesis and reactivity of bridged spiro-epoxyamines.

Michal Szostak1, Jeffrey Aubé.   

Abstract

The first example of a Corey-Chaykovsky epoxidation employing amides as substrates is described. Medium-bridged twisted amides serve as precursors to a family of isolable aminoepoxides. The reactivity of bridged spiro-epoxyamines is also investigated.

Entities:  

Mesh：

Substances：

Year:  2009        PMID： 19715274      PMCID： PMC2753969          DOI： 10.1021/ja906471q

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


  10 in total

1.  Chemo- and Regioselective Conversion of Epoxides to Carbonyl Compounds in 5 M Lithium Perchlorate-Diethyl Ether Medium.

Authors:  R. Sudha; K. Malola Narasimhan; V. Geetha Saraswathy; S. Sankararaman
Journal:  J Org Chem       Date:  1996-03-08       Impact factor: 4.354

2.  Advances in homogeneous and heterogeneous catalytic asymmetric epoxidation.

Authors:  Q-H Xia; H-Q Ge; C-P Ye; Z-M Liu; K-X Su
Journal:  Chem Rev       Date:  2005-05       Impact factor: 60.622

3.  The twisted amide 2-quinuclidone: 60 years in the making.

Authors:  Jonathan Clayden; Wesley J Moran
Journal:  Angew Chem Int Ed Engl       Date:  2006-11-06       Impact factor: 15.336

4.  Cation-pi control of regiochemistry of intramolecular schmidt reactions en route to bridged bicyclic lactams.

Authors:  Lei Yao; Jeffrey Aubé
Journal:  J Am Chem Soc       Date:  2007-02-16       Impact factor: 15.419

5.  Facile C-N cleavage in a series of bridged lactams.

Authors:  Yao Lei; Aaron D Wrobleski; Jennifer E Golden; Douglas R Powell; Jeffrey Aubé
Journal:  J Am Chem Soc       Date:  2005-04-06       Impact factor: 15.419

6.  Synthesis and structural analysis of 2-quinuclidonium tetrafluoroborate.

Authors:  Kousuke Tani; Brian M Stoltz
Journal:  Nature       Date:  2006-06-08       Impact factor: 49.962

7.  Stability of medium-bridged twisted amides in aqueous solutions.

Authors:  Michal Szostak; Lei Yao; Jeffrey Aubé
Journal:  J Org Chem       Date:  2009-03-06       Impact factor: 4.354

8.  A strategy for the solid-phase synthesis of oligosaccharides.

Authors:  S J Danishefsky; K F McClure; J T Randolph; R B Ruggeri
Journal:  Science       Date:  1993-05-28       Impact factor: 47.728

9.  Improved procedure for the synthesis of enamine N-oxides.

Authors:  David Bernier; Alexander J Blake; Simon Woodward
Journal:  J Org Chem       Date:  2008-05-07       Impact factor: 4.354

10.  Catalytic, asymmetric sulfur ylide-mediated epoxidation of carbonyl compounds: scope, selectivity, and applications in synthesis.

Authors:  Varinder K Aggarwal; Caroline L Winn
Journal:  Acc Chem Res       Date:  2004-08       Impact factor: 22.384
  10 in total
  6 in total

Review 1.  Chemistry of bridged lactams and related heterocycles.

Authors:  Michal Szostak; Jeffrey Aubé
Journal:  Chem Rev       Date:  2013-06-17       Impact factor: 60.622

2.  Synthesis, structural analysis, and reactivity of bridged orthoamides by intramolecular Schmidt reaction.

Authors:  Michal Szostak; Jeffrey Aubé
Journal:  J Am Chem Soc       Date:  2010-03-03       Impact factor: 15.419

3.  An efficient computational model to predict protonation at the amide nitrogen and reactivity along the C-N rotational pathway.

Authors:  Roman Szostak; Jeffrey Aubé; Michal Szostak
Journal:  Chem Commun (Camb)       Date:  2015-04-14       Impact factor: 6.222

4.  Synthesis of medium-bridged twisted lactams via cation-pi control of the regiochemistry of the intramolecular Schmidt reaction.

Authors:  Michal Szostak; Lei Yao; Jeffrey Aubé
Journal:  J Org Chem       Date:  2010-02-19       Impact factor: 4.354

5.  Proximity effects in nucleophilic addition reactions to medium-bridged twisted lactams: remarkably stable tetrahedral intermediates.

Authors:  Michal Szostak; Lei Yao; Jeffrey Aubé
Journal:  J Am Chem Soc       Date:  2010-02-17       Impact factor: 15.419

6.  Resonance promoted ring-opening metathesis polymerization of twisted amides.

Authors:  Mizhi Xu; Krista K Bullard; Aja M Nicely; Will R Gutekunst
Journal:  Chem Sci       Date:  2019-08-30       Impact factor: 9.825
  6 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.