Literature DB >> 22489740

Stereocontrolled 1,3-phosphatyloxy and 1,3-halogen migration relay toward highly functionalized 1,3-dienes.

Roohollah Kazem Shiroodi1, Alexander S Dudnik, Vladimir Gevorgyan.   

Abstract

A double migratory cascade reaction of α-halogen-substituted propargylic phosphates to produce highly functionalized 1,3-dienes has been developed. This transformation features 1,3-phosphatyloxy group migration followed by 1,3-shifts of bromine and chlorine as well as the unprecedented 1,3-migration of iodine. The reaction is stereodivergent: (Z)-1,3-dienes are formed in the presence of a copper catalyst, whereas gold-catalyzed reactions exhibit inverted stereoselectivity, producing the corresponding E products.

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Year:  2012        PMID： 22489740      PMCID： PMC3376387          DOI： 10.1021/ja301243t

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


  43 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.  Gold-catalyzed 1,2-migration of silicon, tin, and germanium en route to C-2 substituted fused pyrrole-containing heterocycles.

Authors:  Ilya V Seregin; Vladimir Gevorgyan
Journal:  J Am Chem Soc       Date:  2006-09-20       Impact factor: 15.419

3.  Halogen dance reactions--a review.

Authors:  Michael Schnürch; Markus Spina; Ather Farooq Khan; Marko D Mihovilovic; Peter Stanetty
Journal:  Chem Soc Rev       Date:  2007-03-06       Impact factor: 54.564

4.  Gold-catalyzed 1,3-addition of a sp3-hybridized C-H bond to alkenylcarbenoid intermediate.

Authors:  Sabyasachi Bhunia; Rai-Shung Liu
Journal:  J Am Chem Soc       Date:  2008-12-10       Impact factor: 15.419

5.  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

6.  Concise synthesis of spirocyclic, bridged gamma-butyrolactones via stereospecific, dyotropic rearrangements of beta-lactones involving 1,2-acyl and delta-lactone migrations.

Authors:  Vikram C Purohit; Andrea S Matla; Daniel Romo
Journal:  J Am Chem Soc       Date:  2008-07-16       Impact factor: 15.419

7.  Platinum and ruthenium chloride-catalyzed cycloisomerization of 1-alkyl-2-ethynylbenzenes: interception of pi-activated alkynes with a benzylic C-H bond.

Authors:  Mamoru Tobisu; Hiromi Nakai; Naoto Chatani
Journal:  J Org Chem       Date:  2009-08-07       Impact factor: 4.354

8.  Metal-catalyzed 1,2-shift of diverse migrating groups in allenyl systems as a new paradigm toward densely functionalized heterocycles.

Authors:  Alexander S Dudnik; Anna W Sromek; Marina Rubina; Joseph T Kim; Alexander V Kel'in; Vladimir Gevorgyan
Journal:  J Am Chem Soc       Date:  2008-01-04       Impact factor: 15.419

9.  Mechanistically diverse copper-, silver-, and gold-catalyzed acyloxy and phosphatyloxy migrations: efficient synthesis of heterocycles via cascade migration/cycloisomerization approach.

Authors:  Todd Schwier; Anna W Sromek; Dahrika M L Yap; Dmitri Chernyak; Vladimir Gevorgyan
Journal:  J Am Chem Soc       Date:  2007-07-21       Impact factor: 15.419

10.  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
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  7 in total

1.  A new reactivity mode for the diazo group: diastereoselective 1,3-aminoalkylation reaction of β-amino-α-diazoesters to give triazolines.

Authors:  Alexey Kuznetsov; Anton V Gulevich; Donald J Wink; Vladimir Gevorgyan
Journal:  Angew Chem Int Ed Engl       Date:  2014-07-01       Impact factor: 15.336

2.  Synthesis of furans and pyrroles via migratory and double migratory cycloisomerization reactions of homopropargylic aldehydes and imines.

Authors:  Roohollah Kazem Shiroodi; Claudia I Rivera Vera; Alexander S Dudnik; Vladimir Gevorgyan
Journal:  Tetrahedron Lett       Date:  2015-06-03       Impact factor: 2.415

Review 3.  Metal-catalyzed double migratory cascade reactions of propargylic esters and phosphates.

Authors:  Roohollah Kazem Shiroodi; Vladimir Gevorgyan
Journal:  Chem Soc Rev       Date:  2013-06-21       Impact factor: 54.564

4.  Copper-catalyzed recycling of halogen activating groups via 1,3-halogen migration.

Authors:  R David Grigg; Ryan Van Hoveln; Jennifer M Schomaker
Journal:  J Am Chem Soc       Date:  2012-09-19       Impact factor: 15.419

Review 5.  Modern Synthetic Methods for the Stereoselective Construction of 1,3-Dienes.

Authors:  Raquel G Soengas; Humberto Rodríguez-Solla
Journal:  Molecules       Date:  2021-01-06       Impact factor: 4.411

6.  1,2-boryl migration empowers regiodivergent synthesis of borylated furans.

Authors:  Roohollah Kazem Shiroodi; Olesja Koleda; Vladimir Gevorgyan
Journal:  J Am Chem Soc       Date:  2014-09-10       Impact factor: 15.419

7.  Gold-catalyzed 1,3-transposition of ynones.

Authors:  Roohollah Kazem Shiroodi; Mohammad Soltani; Vladimir Gevorgyan
Journal:  J Am Chem Soc       Date:  2014-07-02       Impact factor: 15.419
  7 in total

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