Literature DB >> 17295496

Gold(I)-catalyzed isomerization of allenyl carbinol esters: an efficient access to functionalized 1,3-butadien-2-ol esters.

Andrea K Buzas1, Florin M Istrate, Fabien Gagosz.   

Abstract

A study concerning the gold(I)-catalyzed rearrangement of diversely substituted allenyl carbinol esters into functionalized 1,3-butadien-2-ol esters is described. The mild conditions employed allow the efficient, rapid, and stereoselective synthesis of a variety of such compounds via a new 1,3-shift of an ester moiety onto a gold-activated allene. [structure: see text]

Entities:  

Year:  2007        PMID： 17295496     DOI： 10.1021/ol063031t

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


  13 in total

1.  Copper-, Silver-, and Gold-Catalyzed Migratory Cycloisomerizations Leading to Heterocyclic Five-Membered Rings.

Authors:  Alexander S Dudnik; Natalia Chernyak; Vladimir Gevorgyan
Journal:  Aldrichimica Acta       Date:  2010       Impact factor: 3.667

2.  The use of Br/Cl to promote regioselective gold-catalyzed rearrangement of propargylic carboxylates: an efficient synthesis of (1Z, 3E)-1-bromo/chloro-2-carboxy-1,3-dienes.

Authors:  Yanzhao Wang; Biao Lu; Liming Zhang
Journal:  Chem Commun (Camb)       Date:  2010-10-29       Impact factor: 6.222

3.  Gold(I)-Catalyzed Hydration of Allenes.

Authors:  Zhibin Zhang; Seong Du Lee; Aaron S Fisher; Ross A Widenhoefer
Journal:  Tetrahedron       Date:  2009-02-28       Impact factor: 2.457

4.  Gold(I)-catalyzed synthesis of (1E,3E)-dienes from propargylic esters.

Authors:  Alexander S Dudnik; Todd Schwier; Vladimir Gevorgyan
Journal:  J Organomet Chem       Date:  2009-02-15       Impact factor: 2.369

5.  Studies toward the unique pederin family member psymberin: full structure elucidation, two alternative total syntheses, and analogs.

Authors:  Yu Feng; Xin Jiang; Jef K De Brabander
Journal:  J Am Chem Soc       Date:  2012-10-04       Impact factor: 15.419

6.  Regio- and stereoselective isomerizations of allenamides: synthesis of 2-amido-dienes and their tandem isomerization-electrocyclic ring-closure.

Authors:  Ryuji Hayashi; Richard P Hsung; John B Feltenberger; Andrew G Lohse
Journal:  Org Lett       Date:  2009-05-21       Impact factor: 6.005

7.  Gold-catalyzed double migration-benzannulation cascade toward naphthalenes.

Authors:  Alexander S Dudnik; Todd Schwier; Vladimir Gevorgyan
Journal:  Org Lett       Date:  2008-03-01       Impact factor: 6.005

Review 8.  Ligand effects in homogeneous Au catalysis.

Authors:  David J Gorin; Benjamin D Sherry; F Dean Toste
Journal:  Chem Rev       Date:  2008-07-25       Impact factor: 60.622

9.  An efficient and practical entry to 2-amido-dienes and 3-amido-trienes from allenamides through stereoselective 1,3-hydrogen shifts.

Authors:  Ryuji Hayashi; John B Feltenberger; Andrew G Lohse; Mary C Walton; Richard P Hsung
Journal:  Beilstein J Org Chem       Date:  2011-04-07       Impact factor: 2.883

10.  Gold-catalyzed regioselective oxidation of terminal allenes: formation of α-methanesulfonyloxy methyl ketones.

Authors:  Yingdong Luo; Guozhu Zhang; Erik S Hwang; Thomas A Wilcoxon; Liming Zhang
Journal:  Beilstein J Org Chem       Date:  2011-05-11       Impact factor: 2.883
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