Literature DB >> 19788297

Intramolecular oxamidation of unsaturated O-alkyl hydroxamates: a remarkably versatile entry to hydroxy lactams.

Duncan J Wardrop1, Edward G Bowen, Raymond E Forslund, Adam D Sussman, Samanthi L Weerasekera.   

Abstract

The development of a versatile method for the preparation of five- to eight-membered hydroxy lactams that involves the iodine(III)-mediated oxamidation of unsaturated O-alkyl hydroxamates is described. This transformation, which is believed to proceed through the intermediacy of singlet nitrenium and bicyclic N-acyl-N-alkoxyaziridinium ions, is both stereospecific and highly regioselective in most of the 22 cases examined.

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Year:  2010        PMID： 19788297      PMCID： PMC2812663          DOI： 10.1021/ja9069997

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


  9 in total

1.  N-methoxy-N-acylnitrenium ions: application to the formal synthesis of (-)-TAN1251A.

Authors:  D J Wardrop; A Basak
Journal:  Org Lett       Date:  2001-04-05       Impact factor: 6.005

2.  N-methoxy-N-acylnitrenium ions: application to the formal synthesis of (+/-)-desmethylamino FR901483.

Authors:  D J Wardrop; W Zhang
Journal:  Org Lett       Date:  2001-07-26       Impact factor: 6.005

3.  Palladium-catalyzed ring-forming aminoacetoxylation of alkenes.

Authors:  Erik J Alexanian; Chulbom Lee; Erik J Sorensen
Journal:  J Am Chem Soc       Date:  2005-06-01       Impact factor: 15.419

4.  Copper catalyzed enantioselective intramolecular aminooxygenation of alkenes.

Authors:  Peter H Fuller; Jin-Woo Kim; Sherry R Chemler
Journal:  J Am Chem Soc       Date:  2008-12-31       Impact factor: 15.419

5.  Total synthesis of (-)-dysibetaine via a nitrenium ion cyclization-dienone cleavage strategy.

Authors:  Duncan J Wardrop; Matthew S Burge
Journal:  Chem Commun (Camb)       Date:  2004-04-27       Impact factor: 6.222

6.  Scope and mechanism of intramolecular aziridination of cyclopent-3-enyl-methylamines to 1-azatricyclo[2.2.1.0(2,6)]heptanes with lead tetraacetate.

Authors:  Huayou Hu; Juan A Faraldos; Robert M Coates
Journal:  J Am Chem Soc       Date:  2009-08-26       Impact factor: 15.419

7.  Metal-free oxidative cyclization of urea-tethered alkenes with hypervalent iodine.

Authors:  Brian M Cochran; Forrest E Michael
Journal:  Org Lett       Date:  2008-10-09       Impact factor: 6.005

8.  Tethered aminohydroxylation (TA) reaction of amides.

Authors:  Timothy J Donohoe; Cedric K A Callens; Amber L Thompson
Journal:  Org Lett       Date:  2009-06-04       Impact factor: 6.005

9.  An experimental and computational approach to defining structure/reactivity relationships for intramolecular addition reactions to bicyclic epoxonium ions.

Authors:  Shuangyi Wan; Hakan Gunaydin; K N Houk; Paul E Floreancig
Journal:  J Am Chem Soc       Date:  2007-06-05       Impact factor: 15.419
  9 in total
  17 in total

Review 1.  Allylic azides: synthesis, reactivity, and the Winstein rearrangement.

Authors:  Angela S Carlson; Joseph J Topczewski
Journal:  Org Biomol Chem       Date:  2019-05-08       Impact factor: 3.876

2.  Photocatalytic Oxyamination of Alkenes: Copper(II) Salts as Terminal Oxidants in Photoredox Catalysis.

Authors:  Nicholas L Reed; Madeline I Herman; Vladimir P Miltchev; Tehshik P Yoon
Journal:  Org Lett       Date:  2018-11-08       Impact factor: 6.005

3.  Nitrenium ion-mediated alkene bis-cyclofunctionalization: total synthesis of (-)-swainsonine.

Authors:  Duncan J Wardrop; Edward G Bowen
Journal:  Org Lett       Date:  2011-04-12       Impact factor: 6.005

4.  Copper-Catalyzed Modular Amino Oxygenation of Alkenes: Access to Diverse 1,2-Amino Oxygen-Containing Skeletons.

Authors:  Brett N Hemric; Andy W Chen; Qiu Wang
Journal:  J Org Chem       Date:  2019-01-17       Impact factor: 4.354

5.  Diastereoselective nitrenium ion-mediated cyclofunctionalization: total synthesis of (+)-castanospermine.

Authors:  Edward G Bowen; Duncan J Wardrop
Journal:  Org Lett       Date:  2010-10-21       Impact factor: 6.005

6.  Stereoselective synthesis of F-ring saturated estrone-derived inhibitors of Hedgehog signaling based on cyclopamine.

Authors:  Zhihui Zhang; Valérie Baubet; Christian Ventocilla; Chaomei Xiang; Nadia Dahmane; Jeffrey D Winkler
Journal:  Org Lett       Date:  2011-08-15       Impact factor: 6.005

7.  Ligand Controlled Ir-Catalyzed Regiodivergent Oxyamination of Unactivated Alkenes.

Authors:  Honghui Lei; John H Conway; Caleb C Cook; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2019-07-16       Impact factor: 15.419

8.  Mechanistic analysis and optimization of the copper-catalyzed enantioselective intramolecular alkene aminooxygenation.

Authors:  Monissa C Paderes; Jerome B Keister; Sherry R Chemler
Journal:  J Org Chem       Date:  2012-12-28       Impact factor: 4.354

9.  Methods for direct alkene diamination, new & old.

Authors:  Sam de Jong; Daniel G Nosal; Duncan J Wardrop
Journal:  Tetrahedron       Date:  2012-03-21       Impact factor: 2.457

10.  Iron catalyzed asymmetric oxyamination of olefins.

Authors:  Kevin S Williamson; Tehshik P Yoon
Journal:  J Am Chem Soc       Date:  2012-07-23       Impact factor: 15.419
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