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Literature DB >> 19161306

Asymmetric synthesis of medium-sized rings by intramolecular Au(I)-catalyzed cyclopropanation.

Iain D G Watson¹, Stefanie Ritter, F Dean Toste.

Abstract

An efficient method for the asymmetric gold(I)-catalyzed preparation of medium sized rings has been developed. The method provides 7- to 9-membered rings in excellent yield. High enantioselectivities can be achieved for 7- and 8-membered ring products employing chiral gold(I) complexes. The results provide insight into the mechanism, showing the fluxional nature of gold(I)-stabilized vinyl carbenoid intermediates.

Entities: Chemical Species

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Year: 2009 PMID： 19161306 PMCID： PMC2662771 DOI： 10.1021/ja8085005

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

36 in total

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Journal: Proc Natl Acad Sci U S A Date: 2004-03-31 Impact factor: 11.205

2. Molecular diversity through gold catalysis with alkynes.

Authors: Eloísa Jiménez-Núñez; Antonio M Echavarren
Journal: Chem Commun (Camb) Date: 2006-11-09 Impact factor: 6.222

Review 3. Relativistic effects in homogeneous gold catalysis.

Authors: David J Gorin; F Dean Toste
Journal: Nature Date: 2007-03-22 Impact factor: 49.962

Review 4. Gold-catalyzed cycloisomerizations of enynes: a mechanistic perspective.

Authors: Eloísa Jiménez-Núñez; Antonio M Echavarren
Journal: Chem Rev Date: 2008-07-18 Impact factor: 60.622

5. Gold(I)-catalyzed stereoselective olefin cyclopropanation.

Authors: Magnus J Johansson; David J Gorin; Steven T Staben; F Dean Toste
Journal: J Am Chem Soc Date: 2005-12-28 Impact factor: 15.419

6. 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

7. Highly Enantioselective Palladium-Catalyzed Ene-Type Cyclization of a 1,6-Enyne We are grateful to Drs. H. Kumobayashi, T. Miura, and N. Sayo of Takasago International Co. for providing the BINAP and SEGPHOS ligands. We also thank Dr. M. Yamasaki and Mr. S. Sato of RIGAKU Co. for the X-ray analyses.

Authors: Manabu Hatano; Masahiro Terada; Koichi Mikami
Journal: Angew Chem Int Ed Engl Date: 2001-01-05 Impact factor: 15.336

8. New insights on the mechanism of the transition-metal stereoselective olefin cyclopropanation.

Authors: Elena Soriano; José Marco-Contelles
Journal: Chemistry Date: 2008 Impact factor: 5.236

9. Fluorenes and styrenes by Au(I)-catalyzed annulation of enynes and alkynes.

Authors: David J Gorin; Iain D G Watson; F Dean Toste
Journal: J Am Chem Soc Date: 2008-03-06 Impact factor: 15.419

10. Chiral biphenyl diphosphines for asymmetric catalysis: stereoelectronic design and industrial perspectives.

Authors: Séverine Jeulin; Sébastien Duprat de Paule; Virginie Ratovelomanana-Vidal; Jean-Pierre Genêt; Nicolas Champion; Philippe Dellis
Journal: Proc Natl Acad Sci U S A Date: 2004-03-18 Impact factor: 11.205

27 in total

1. Gold(I)-catalyzed enantioselective [3+2] and [3+3] cycloaddition reactions of propargyl acetals/ketals.

Authors: Cristina Navarro; Nathan D Shapiro; Maurizio Bernasconi; Takahiro Horibe; F Dean Toste
Journal: Tetrahedron Date: 2015-09-02 Impact factor: 2.457

2. Gold(I)-Catalyzed Desymmetrization of 1,4-Dienes by an Enantioselective Tandem Alkoxylation/Claisen Rearrangement.

Authors: Hongmiao Wu; Weiwei Zi; Guigen Li; Hongjian Lu; F Dean Toste
Journal: Angew Chem Int Ed Engl Date: 2015-06-01 Impact factor: 15.336

3. Rhodium-catalyzed intra- and intermolecular [5 + 2] cycloaddition of 3-acyloxy-1,4-enyne and alkyne with concomitant 1,2-acyloxy migration.

Authors: Xing-Zhong Shu; Xiaoxun Li; Dongxu Shu; Suyu Huang; Casi M Schienebeck; Xin Zhou; Patrick J Robichaux; Weiping Tang
Journal: J Am Chem Soc Date: 2012-03-12 Impact factor: 15.419

4. Studies Targeting Ryanodol Result in an Annulation Reaction for the Synthesis of a Variety of Fused Carbocycles.

Authors: Rajdip Karmakar; Arnold L Rheingold; Glenn C Micalizio
Journal: Org Lett Date: 2019-07-12 Impact factor: 6.005

5. Wolff/Cope Approach to the AB Ring of the Sesterterpenoid Variecolin.

Authors: Michael R Krout; Christopher E Henry; Thomas Jensen; Kun-Liang Wu; Scott C Virgil; Brian M Stoltz
Journal: J Org Chem Date: 2018-01-23 Impact factor: 4.354

6. Interception of a Rautenstrauch intermediate by alkynes for [5+2] cycloaddition: rhodium-catalyzed cycloisomerization of 3-acyloxy-4-ene-1,9-diynes to bicyclo[5.3.0]decatrienes.

Authors: Xing-zhong Shu; Suyu Huang; Dongxu Shu; Ilia A Guzei; Weiping Tang
Journal: Angew Chem Int Ed Engl Date: 2011-07-11 Impact factor: 15.336

Review 7. Rhodium-catalyzed acyloxy migration of propargylic esters in cycloadditions, inspiration from the recent "gold rush".

Authors: Xing-Zhong Shu; Dongxu Shu; Casi M Schienebeck; Weiping Tang
Journal: Chem Soc Rev Date: 2012-12-07 Impact factor: 54.564