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Literature DB >> 16366541

Gold(I)-catalyzed stereoselective olefin cyclopropanation.

Magnus J Johansson¹, David J Gorin, Steven T Staben, F Dean Toste.

Abstract

A triphenylphosphinegold(I)-catalyzed cyclopropanation of olefins using propargyl esters as gold(I)-carbene precursors is reported. This reaction provided the basis for the use of a DTBM-SEGPHOS gold(I) complex as a catalyst in the enantioselective (up to 94% ee) preparation of vinyl cyclopropanes with high cis-selectivity.

Entities: Chemical

Mesh：

Substances：
Alkenes
Cyclopropanes
Gold

Year: 2005 PMID： 16366541 DOI： 10.1021/ja0552500

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

Keyword Cloud
Cited

58 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. Supramolecular catalysis: A rotaxane with the golden touch.

Authors: Ai-Lan Lee
Journal: Nat Chem Date: 2015-11-23 Impact factor: 24.427

3. 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

4. The use of Br/Cl to promote regioselective gold-catalyzed rearrangement of propargylic carboxylates: an efficient synthesis of (1Z, 3E)-1-bromo/chloro-2-carboxy-1,3-dienes.

Authors: Yanzhao Wang; Biao Lu; Liming Zhang
Journal: Chem Commun (Camb) Date: 2010-10-29 Impact factor: 6.222

Gold(I)-catalyzed stereoselective olefin cyclopropanation.

1. Copper-, Silver-, and Gold-Catalyzed Migratory Cycloisomerizations Leading to Heterocyclic Five-Membered Rings.

2. Supramolecular catalysis: A rotaxane with the golden touch.

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

4. The use of Br/Cl to promote regioselective gold-catalyzed rearrangement of propargylic carboxylates: an efficient synthesis of (1Z, 3E)-1-bromo/chloro-2-carboxy-1,3-dienes.

5. Gold catalysis: Carbene or cation?

6. Stereodivergent Rhodium(III)-Catalyzed cis-Cyclopropanation Enabled by Multivariate Optimization.

7. Gold(I)-catalyzed enantioselective synthesis of benzopyrans via rearrangement of allylic oxonium intermediates.

8. Gold(I)-catalyzed enantioselective [4 + 2]-cycloaddition of allene-dienes.

Review 9. Metal-catalyzed double migratory cascade reactions of propargylic esters and phosphates.

10. A bonding model for gold(I) carbene complexes.