Literature DB >> 22414252

Carbocyclization cascades of allyl ketenimines via aza-Claisen rearrangements of N-phosphoryl-N-allyl-ynamides.

Kyle A DeKorver1, Xiao-Na Wang, Mary C Walton, Richard P Hsung.   

Abstract

A series of carbocyclization cascades of allyl ketenimines initiated through a thermal aza-Claisen rearrangement of N-phosphoryl-N-allyl ynamides is described. Interceptions of the cationic intermediate via Meerwein-Wagner rearrangements and polyene-type cyclizations en route to fused bi- and tricyclic frameworks are featured.

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Year:  2012        PMID： 22414252      PMCID： PMC3321125          DOI： 10.1021/ol300366e

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


  33 in total

1.  Synthesis of Polyquinane Natural Products: An Update.

Authors:  Goverdhan Mehta; A. Srikrishna
Journal:  Chem Rev       Date:  1997-05-08       Impact factor: 60.622

2.  Cu(I)- and Cu(II)-catalyzed cyclo- and Michael addition reactions of unsaturated β-ketoesters.

Authors:  Christoph Schotes; Antonio Mezzetti
Journal:  J Org Chem       Date:  2011-06-15       Impact factor: 4.354

3.  Synthetic studies in the intramolecular carbocyclization of N-acyloxyiminium ions. Stereoelectronic and steric implications of nucleophilic alkene, alkyne, and allene tethers.

Authors:  Stephen Hanessian; Martin Tremblay; Mauro Marzi; Juan R Del Valle
Journal:  J Org Chem       Date:  2005-06-24       Impact factor: 4.354

4.  Total synthesis of (±)-phomactin A. Lessons learned from respecting a challenging structural topology.

Authors:  Grant S Buchanan; Kevin P Cole; Yu Tang; Richard P Hsung
Journal:  J Org Chem       Date:  2011-08-05       Impact factor: 4.354

5.  Gold-catalyzed oxidative cyclization of 1,5-enynes using external oxidants.

Authors:  Dhananjayan Vasu; Hsiao-Hua Hung; Sabyasachi Bhunia; Sagar Ashok Gawade; Arindam Das; Rai-Shung Liu
Journal:  Angew Chem Int Ed Engl       Date:  2011-06-06       Impact factor: 15.336

6.  Intermolecular and selective synthesis of 2,4,5-trisubstituted oxazoles by a gold-catalyzed formal [3+2] cycloaddition.

Authors:  Paul W Davies; Alex Cremonesi; Lidia Dumitrescu
Journal:  Angew Chem Int Ed Engl       Date:  2011-07-26       Impact factor: 15.336

7.  Synthesis of multisubstituted enamides via Pd-catalyzed chloroallylation of ynamides.

Authors:  Zenghui Lu; Wei Kong; Zheliang Yuan; Xueyan Zhao; Gangguo Zhu
Journal:  J Org Chem       Date:  2011-09-29       Impact factor: 4.354

8.  Gold-catalyzed 1,2-difunctionalizations of aminoalkynes using only N- and O-containing oxidants.

Authors:  Anupam Mukherjee; Ramesh B Dateer; Rupsha Chaudhuri; Sabyasachi Bhunia; Somnath Narayan Karad; Rai-Shung Liu
Journal:  J Am Chem Soc       Date:  2011-09-12       Impact factor: 15.419

9.  Introducing a new class of N-phosphoryl ynamides via Cu(I)-catalyzed amidations of alkynyl bromides.

Authors:  Kyle A DeKorver; Mary C Walton; Troy D North; Richard P Hsung
Journal:  Org Lett       Date:  2011-08-17       Impact factor: 6.005

10.  Total synthesis of phomactin A.

Authors:  Yu Tang; Kevin P Cole; Grant S Buchanan; Gang Li; Richard P Hsung
Journal:  Org Lett       Date:  2009-04-02       Impact factor: 6.005
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  5 in total

1.  An intramolecular [2 + 2] cycloaddition of ketenimines via palladium-catalyzed rearrangements of N-allyl-ynamides.

Authors:  Kyle A DeKorver; Richard P Hsung; Wang-Ze Song; Xiao-Na Wang; Mary C Walton
Journal:  Org Lett       Date:  2012-06-05       Impact factor: 6.005

2.  S3S63 Terminal Ynamides: Synthesis, Coupling Reactions and Additions to Common Electrophiles.

Authors:  Andrea M Cook; Christian Wolf
Journal:  Tetrahedron Lett       Date:  2015-05-06       Impact factor: 2.415

3.  Synthesis of cyclopentenimines from N-allyl ynamides via a tandem aza-Claisen rearrangement-carbocyclization sequence.

Authors:  Xiao-Na Wang; Gabrielle N Winston-McPherson; Mary C Walton; Yu Zhang; Richard P Hsung; Kyle A DeKorver
Journal:  J Org Chem       Date:  2013-06-10       Impact factor: 4.354

4.  Ynamides in ring forming transformations.

Authors:  Xiao-Na Wang; Hyun-Suk Yeom; Li-Chao Fang; Shuzhong He; Zhi-Xiong Ma; Brant L Kedrowski; Richard P Hsung
Journal:  Acc Chem Res       Date:  2013-10-28       Impact factor: 22.384

5.  A Convenient Synthesis of γ-Amino-Ynamides via Additions of Lithiated Ynamides to Aryl Imines. Observation of an Aza-Meyer-Schuster Rearrangement.

Authors:  Rui Qi; Xiao-Na Wang; Kyle A Dekorver; Yu Tang; Chao-Chao Wang; Qian Li; Hui Li; Ming-Can Lv; Qing Yu; Richard P Hsung
Journal:  Synthesis (Stuttg)       Date:  2013-07-01       Impact factor: 3.157
  5 in total

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