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Literature DB >> 18616257

Catalytic enantioselective intermolecular cycloaddition of 2-diazo-3,6-diketoester-derived carbonyl ylides with alkynes and styrenes using chiral dirhodium(II) carboxylates.

Naoyuki Shimada¹, Masahiro Anada, Seiichi Nakamura, Hisanori Nambu, Hideyuki Tsutsui, Shunichi Hashimoto.

Abstract

Dirhodium(II) tetrakis[ N-tetrachlorophthaloyl-( S)- tert-leucinate], Rh 2( S-TCPTTL) 4, is an exceptionally effective catalyst for enantioselective tandem carbonyl ylide formation-cycloaddition reactions of 2-diazo-3,6-diketoesters with arylacetylene, alkoxyacetylene, and styrene dipolarophiles, providing cycloadducts in good to high yields and with enantioselectivities of up to 99% ee as well as with perfect exo diastereoselectivity for styrenes.

Entities: Chemical Gene

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Year: 2008 PMID： 18616257 DOI： 10.1021/ol8013733

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

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Cited

8 in total

1. The chiral crown conformation in paddlewheel complexes.

Authors: Andrew DeAngelis; David T Boruta; Jean-Bernard Lubin; James N Plampin; Glenn P A Yap; Joseph M Fox
Journal: Chem Commun (Camb) Date: 2010-05-11 Impact factor: 6.222

2. Asymmetric synthesis of methylenetetrahydrofurans by palladium-catalyzed [3 + 2] cycloaddition of trimethylenemethane with aldehydes--a novel ligand design.

Authors: Barry M Trost; Dustin A Bringley; Steven M Silverman
Journal: J Am Chem Soc Date: 2011-05-03 Impact factor: 15.419

3. Catalytic asymmetric synthesis of 8-oxabicyclooctanes by intermolecular [5+2] pyrylium cycloadditions.

Authors: Michael R Witten; Eric N Jacobsen
Journal: Angew Chem Int Ed Engl Date: 2014-04-29 Impact factor: 15.336

4. Dual catalysis in enantioselective oxidopyrylium-based [5 + 2] cycloadditions.

Authors: Noah Z Burns; Michael R Witten; Eric N Jacobsen
Journal: J Am Chem Soc Date: 2011-08-25 Impact factor: 15.419

5. Enantioselective synthesis of 2,2-disubstituted tetrahydrofurans: palladium-catalyzed [3+2] cycloadditions of trimethylenemethane with ketones.

Authors: Barry M Trost; Dustin A Bringley
Journal: Angew Chem Int Ed Engl Date: 2013-03-12 Impact factor: 15.336

Catalytic enantioselective intermolecular cycloaddition of 2-diazo-3,6-diketoester-derived carbonyl ylides with alkynes and styrenes using chiral dirhodium(II) carboxylates.

1. The chiral crown conformation in paddlewheel complexes.

2. Asymmetric synthesis of methylenetetrahydrofurans by palladium-catalyzed [3 + 2] cycloaddition of trimethylenemethane with aldehydes--a novel ligand design.

3. Catalytic asymmetric synthesis of 8-oxabicyclooctanes by intermolecular [5+2] pyrylium cycloadditions.

4. Dual catalysis in enantioselective oxidopyrylium-based [5 + 2] cycloadditions.

5. Enantioselective synthesis of 2,2-disubstituted tetrahydrofurans: palladium-catalyzed [3+2] cycloadditions of trimethylenemethane with ketones.

6. Rh(2)(S-PTTL)(3)TPA-A Mixed Ligand Dirhodium(II) Catalyst for Enantioselective Reactions of α-Alkyl-α-Diazoesters.

7. Chiral crown conformation of Rh(2)(S-PTTL)(4): enantioselective cyclopropanation with alpha-alkyl-alpha-diazoesters.

8. Asymmetric syntheses of 8-oxabicyclo[3,2,1]octane and 11-oxatricyclo[5.3.1.0]undecane from glycals.