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Literature DB >> 16288518

Gold-catalyzed cyclization of (Z)-2-en-4-yn-1-ols: highly efficient synthesis of fully substituted dihydrofurans and furans.

Yuanhong Liu¹, Feijie Song, Zhiquan Song, Meina Liu, Bin Yan.

Abstract

[reaction: see text] The gold-catalyzed cyclization of (Z)-enynols offers an efficient and straightforward route to stereodefined (Z)-5-ylidene-2,5-dihydrofurans and fully substituted furans under extremely mild reaction conditions. Importantly, the results indicated that both the oxyauration and the proto-demetalation steps are highly stereoselective.

Entities: Chemical

Year: 2005 PMID： 16288518 DOI： 10.1021/ol052160r

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

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Cited

15 in total

1. Computation-guided development of Au-catalyzed cycloisomerizations proceeding via 1,2-Si or 1,2-H migrations: regiodivergent synthesis of silylfurans.

Authors: Alexander S Dudnik; Yuanzhi Xia; Yahong Li; Vladimir Gevorgyan
Journal: J Am Chem Soc Date: 2010-06-09 Impact factor: 15.419

Review 2. Transition metal-mediated synthesis of monocyclic aromatic heterocycles.

Authors: Anton V Gulevich; Alexander S Dudnik; Natalia Chernyak; Vladimir Gevorgyan
Journal: Chem Rev Date: 2013-01-10 Impact factor: 60.622

3. Enantioselective synthesis of alkyne-substituted quaternary carbon stereogenic centers through NHC-Cu-catalyzed allylic substitution reactions with (i-Bu)2(alkynyl)aluminum reagents.

Authors: Jennifer A Dabrowski; Fang Gao; Amir H Hoveyda
Journal: J Am Chem Soc Date: 2011-03-08 Impact factor: 15.419

4. Total syntheses of bryostatins: synthesis of two ring-expanded bryostatin analogues and the development of a new-generation strategy to access the C7-C27 fragment.

Authors: Barry M Trost; Hanbiao Yang; Guangbin Dong
Journal: Chemistry Date: 2011-07-21 Impact factor: 5.236

5. Intermolecular hydroamination of allenes with N-unsubstituted carbamates catalyzed by a gold(I) N-heterocyclic carbene complex.

Authors: Robert E Kinder; Zhibin Zhang; Ross A Widenhoefer
Journal: Org Lett Date: 2008-06-21 Impact factor: 6.005

Gold-catalyzed cyclization of (Z)-2-en-4-yn-1-ols: highly efficient synthesis of fully substituted dihydrofurans and furans.

1. Computation-guided development of Au-catalyzed cycloisomerizations proceeding via 1,2-Si or 1,2-H migrations: regiodivergent synthesis of silylfurans.

Review 2. Transition metal-mediated synthesis of monocyclic aromatic heterocycles.

3. Enantioselective synthesis of alkyne-substituted quaternary carbon stereogenic centers through NHC-Cu-catalyzed allylic substitution reactions with (i-Bu)2(alkynyl)aluminum reagents.

4. Total syntheses of bryostatins: synthesis of two ring-expanded bryostatin analogues and the development of a new-generation strategy to access the C7-C27 fragment.

5. Intermolecular hydroamination of allenes with N-unsubstituted carbamates catalyzed by a gold(I) N-heterocyclic carbene complex.

6. Total synthesis of bryostatin 16 using atom-economical and chemoselective approaches.

7. Gold-catalyzed oxidation of arylallenes: Synthesis of quinoxalines and benzimidazoles.

8. Gold(I)-catalyzed formation of furans by a Claisen-type rearrangement of ynenyl allyl ethers.

9. Synthesis of oxazocenones via gold(I)-catalyzed 8-endo-dig hydroalkoxylation of alkynamides.

10. Gold-catalyzed intermolecular hydroamination of allenes with sulfonamides.