Literature DB >> 19148263

Efficient route to 4H-1,3-oxazines through ring expansion of isoxazoles by rhodium carbenoids.

James R Manning1, Huw M L Davies.   

Abstract

Studies related to the total synthesis of elisabethin C led to the discovery of a rhodium-catalyzed cascade sequence involving isoxazole ring expansion and a [4 + 3] cycloaddition. The scope of the isoxazole ring expansion was explored, resulting in the synthesis of a range of 4H-1,3-oxazines in 47-96% yield.

Entities:  

Year:  2008        PMID： 19148263      PMCID： PMC2587331          DOI： 10.1016/j.tet.2008.03.010

Source DB:  PubMed          Journal:  Tetrahedron        ISSN： 0040-4020            Impact factor:   2.457


  9 in total

1.  Direct synthesis of (+)-erogorgiaene through a kinetic enantiodifferentiating step.

Authors:  Huw M L Davies; Abbas M Walji
Journal:  Angew Chem Int Ed Engl       Date:  2005-03-04       Impact factor: 15.336

2.  Asymmetric synthesis of tropanes by rhodium-catalyzed [4 + 3] cycloaddition.

Authors:  Ravisekhara P Reddy; Huw M L Davies
Journal:  J Am Chem Soc       Date:  2007-08-08       Impact factor: 15.419

3.  Total synthesis of (+/-)-jiadifenin and studies directed to understanding its SAR: probing mechanistic and stereochemical issues in palladium-mediated allylation of enolate-like structures.

Authors:  David A Carcache; Young Shin Cho; Zihao Hua; Yuan Tian; Yue-Ming Li; Samuel J Danishefsky
Journal:  J Am Chem Soc       Date:  2006-01-25       Impact factor: 15.419

4.  Cardiotonic agents. 1-Methyl-7-(4-pyridyl)-5,6,7,8-tetrahydro-3 (2H)-isoquinolinones and related compounds. Synthesis and activity.

Authors:  T Kaiho; K San-Nohe; S Kajiya; T Suzuki; K Otsuka; T Ito; J Kamiya; M Maruyama
Journal:  J Med Chem       Date:  1989-02       Impact factor: 7.446

5.  Catalytic asymmetric cyclopropanation of heteroaryldiazoacetates.

Authors:  H M Davies; R J Townsend
Journal:  J Org Chem       Date:  2001-10-05       Impact factor: 4.354

6.  Unusual Terpenes with Novel Carbon Skeletons from the West Indian Sea Whip Pseudopterogorgia elisabethae (Octocorallia)(1).

Authors:  Abimael D. Rodríguez; Eduvigis González; Songping D. Huang
Journal:  J Org Chem       Date:  1998-10-02       Impact factor: 4.354

7.  Highly diastereoselective and enantioselective C-H functionalization of 1,2-dihydronaphthalenes: a combined C-H activation/Cope rearrangement followed by a retro-Cope rearrangement.

Authors:  Huw M L Davies; Qihui Jin
Journal:  J Am Chem Soc       Date:  2004-09-08       Impact factor: 15.419

8.  Combined C-H activation/cope rearrangement as a strategic reaction in organic synthesis: total synthesis of (-)-colombiasin a and (-)-elisapterosin B.

Authors:  Huw M L Davies; Xing Dai; Matthew S Long
Journal:  J Am Chem Soc       Date:  2006-02-22       Impact factor: 15.419

9.  Catalytic asymmetric reactions for organic synthesis: the combined C-H activation/Cope rearrangement.

Authors:  Huw M L Davies; Qihui Jin
Journal:  Proc Natl Acad Sci U S A       Date:  2004-03-15       Impact factor: 11.205
  9 in total
  4 in total

1.  Multifunctionalized 3-hydroxypyrroles in a three-step, one-pot cascade process from methyl 3-TBSO-2-diazo-3-butenoate and nitrones.

Authors:  Xinfang Xu; Maxim O Ratnikov; Peter Y Zavalij; Michael P Doyle
Journal:  Org Lett       Date:  2011-10-27       Impact factor: 6.005

2.  Au-catalyzed skeletal rearrangement of O-propargylic oximes via N-O bond cleavage with the aid of a Brønsted base cocatalyst.

Authors:  Keigo Shiga; Ilya D Gridnev; Masahiro Terada; Itaru Nakamura
Journal:  Chem Sci       Date:  2019-04-18       Impact factor: 9.825

3.  Isoxazolium N-ylides and 1-oxa-5-azahexa-1,3,5-trienes on the way from isoxazoles to 2H-1,3-oxazines.

Authors:  Alexander F Khlebnikov; Mikhail S Novikov; Yelizaveta G Gorbunova; Ekaterina E Galenko; Kirill I Mikhailov; Viktoriia V Pakalnis; Margarita S Avdontceva
Journal:  Beilstein J Org Chem       Date:  2014-08-14       Impact factor: 2.883

4.  Gold-catalyzed (4 + 2)-annulations between α-alkyl alkenylgold carbenes and benzisoxazoles with reactive alkyl groups.

Authors:  Bhanudas Dattatray Mokar; Prakash D Jadhav; Y B Pandit; Rai-Shung Liu
Journal:  Chem Sci       Date:  2018-04-23       Impact factor: 9.825
  4 in total

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