Literature DB >> 11483054

Gold(III) chloride catalyzed cyclization of alpha-hydroxyallenes to 2,5-dihydrofurans.

A Hoffmann-Röder1, N Krause.   

Abstract

[reaction: see text] Functionalized alpha-hydroxyallenes 1 were smoothly converted into the corresponding 2,5-dihydrofurans 2 by using 5-10 mol % of gold(III) chloride as catalyst. This mild and efficient cyclization method can be applied to alkyl- and alkenyl-substituted allenes at room temperature, furnishing tri- and tetrasubstituted dihydrofurans in good to excellent chemical yields and with complete axis to center chirality transfer.

Entities:  

Year:  2001        PMID: 11483054     DOI: 10.1021/ol016205+

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


  20 in total

1.  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

2.  1,2-Halogen migration in haloallenyl ketones: regiodivergent synthesis of halofurans.

Authors:  Anna W Sromek; Marina Rubina; Vladimir Gevorgyan
Journal:  J Am Chem Soc       Date:  2005-08-03       Impact factor: 15.419

3.  Enantioselective Synthesis of Allenes by Catalytic Traceless Petasis Reactions.

Authors:  Yao Jiang; Abdallah B Diagne; Regan J Thomson; Scott E Schaus
Journal:  J Am Chem Soc       Date:  2017-01-25       Impact factor: 15.419

4.  Multisubstituted N-fused heterocycles via transition metal-catalyzed cycloisomerization protocols.

Authors:  Ilya V Seregin; Alex W Schammel; Vladimir Gevorgyan
Journal:  Tetrahedron       Date:  2008-07-14       Impact factor: 2.457

5.  (1R,4'S)-4-(tert-Butyl-dimethyl-silan-oxy)-1-[2,2-dimethyl-3-(p-tolyl-sulfon-yl)-1,3-oxazolidin-4-yl]but-2-yn-1-ol.

Authors:  Jörg Erdsack; Markus Schürmann; Hans Preut; Norbert Krause
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-05-30

6.  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

7.  Scope and mechanistic analysis of the enantioselective synthesis of allenes by rhodium-catalyzed tandem ylide formation/[2,3]-sigmatropic rearrangement between donor/acceptor carbenoids and propargylic alcohols.

Authors:  Zhanjie Li; Vyacheslav Boyarskikh; Jørn H Hansen; Jochen Autschbach; Djamaladdin G Musaev; Huw M L Davies
Journal:  J Am Chem Soc       Date:  2012-09-11       Impact factor: 15.419

8.  Mechanistic insights into the gold-catalyzed cycloisomerization of bromoallenyl ketones: ligand-controlled regioselectivity.

Authors:  Yuanzhi Xia; Alexander S Dudnik; Vladimir Gevorgyan; Yahong Li
Journal:  J Am Chem Soc       Date:  2008-05-08       Impact factor: 15.419

Review 9.  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

10.  Exploiting hidden symmetry in natural products: total syntheses of amphidinolides C and F.

Authors:  Subham Mahapatra; Rich G Carter
Journal:  J Am Chem Soc       Date:  2013-07-11       Impact factor: 15.419

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