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Literature DB >> 19719176

Gold-catalyzed intermolecular Markovnikov hydroamination of allenes with secondary amines.

Xiaoming Zeng¹, Michele Soleilhavoup, Guy Bertrand.

Abstract

A cationic (CAAC)gold(I) complex promotes the addition of all types of nontertiary amines to a variety of allenes, affording allylic amines in good to excellent yields; the amino fragment always adds to the less substituted terminus of the CCC skeleton.

Entities: Chemical Disease Gene Species

Mesh：

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Year: 2009 PMID： 19719176 PMCID： PMC2739117 DOI： 10.1021/ol901418c

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

38 in total

1. Enantioselective catalytic hydroamination of alkenes.

Authors: Peter W Roesky; Thomas E Müller
Journal: Angew Chem Int Ed Engl Date: 2003-06-23 Impact factor: 15.336

Review 2. Transition-metal-catalyzed addition of heteroatom-hydrogen bonds to alkynes.

Authors: Francisco Alonso; Irina P Beletskaya; Miguel Yus
Journal: Chem Rev Date: 2004-06 Impact factor: 60.622

Review 3. Asymmetric hydroamination of non-activated carbon-carbon multiple bonds.

Authors: Isabelle Aillaud; Jacqueline Collin; Jérôme Hannedouche; Emmanuelle Schulz
Journal: Dalton Trans Date: 2007-09-07 Impact factor: 4.390

4. Gold-catalyzed organic reactions.

Authors: A Stephen K Hashmi
Journal: Chem Rev Date: 2007-06-20 Impact factor: 60.622

5. Gold(I)-catalyzed dynamic kinetic enantioselective intramolecular hydroamination of allenes.

Authors: Zhibin Zhang; Christopher F Bender; Ross A Widenhoefer
Journal: J Am Chem Soc Date: 2007-10-30 Impact factor: 15.419

Review 6. Hydroamination: direct addition of amines to alkenes and alkynes.

Authors: Thomas E Müller; Kai C Hultzsch; Miguel Yus; Francisco Foubelo; Mizuki Tada
Journal: Chem Rev Date: 2008-08-26 Impact factor: 60.622

7. Homogeneous catalytic hydroamination of alkynes and allenes with ammonia.

Authors: Vincent Lavallo; Guido D Frey; Bruno Donnadieu; Michele Soleilhavoup; Guy Bertrand
Journal: Angew Chem Int Ed Engl Date: 2008 Impact factor: 15.336

8. Recent developments in enantioselective gold(I) catalysis.

Authors: Ross A Widenhoefer
Journal: Chemistry Date: 2008 Impact factor: 5.236

9. Intramolecular "hydroiminiumation and -amidiniumation" of alkenes: a convenient, flexible, and scalable route to cyclic iminium and imidazolinium salts.

Authors: Rodolphe Jazzar; Jean-Baptiste Bourg; Rian D Dewhurst; Bruno Donnadieu; Guy Bertrand
Journal: J Org Chem Date: 2007-04-05 Impact factor: 4.354

10. Golden opportunities in natural product synthesis: first total synthesis of (-)-isocyclocapitelline and (-)-isochrysotricine by gold-catalyzed allene cycloisomerization.

Authors: Frank Volz; Norbert Krause
Journal: Org Biomol Chem Date: 2007-04-16 Impact factor: 3.876

15 in total

Gold-catalyzed intermolecular Markovnikov hydroamination of allenes with secondary amines.

1. Enantioselective catalytic hydroamination of alkenes.

Review 2. Transition-metal-catalyzed addition of heteroatom-hydrogen bonds to alkynes.

Review 3. Asymmetric hydroamination of non-activated carbon-carbon multiple bonds.

4. Gold-catalyzed organic reactions.

5. Gold(I)-catalyzed dynamic kinetic enantioselective intramolecular hydroamination of allenes.

Review 6. Hydroamination: direct addition of amines to alkenes and alkynes.

7. Homogeneous catalytic hydroamination of alkynes and allenes with ammonia.

8. Recent developments in enantioselective gold(I) catalysis.

9. Intramolecular "hydroiminiumation and -amidiniumation" of alkenes: a convenient, flexible, and scalable route to cyclic iminium and imidazolinium salts.

10. Golden opportunities in natural product synthesis: first total synthesis of (-)-isocyclocapitelline and (-)-isochrysotricine by gold-catalyzed allene cycloisomerization.

1. A Brief Survey of our Contribution to Stable Carbene Chemistry.

2. Mechanistic study of gold(I)-catalyzed intermolecular hydroamination of allenes.

3. Gold(I)-Catalyzed Intermolecular Hydroamination of Allenes with Arylamines.

Review 4. Stable cyclic carbenes and related species beyond diaminocarbenes.

5. Platinum(II)-catalyzed intermolecular hydroamination of monosubstituted allenes with secondary alkylamines.

6. Gold(I)-Catalyzed Enantioselective Intramolecular Hydroamination of Allenes with Ureas.

7. Gold(I)-catalyzed stereoconvergent, intermolecular enantioselective hydroamination of allenes.

8. Synthesis of a room-temperature-stable dimeric copper(I) hydride.

9. Regio- and enantioselective hydroamination of dienes by gold(I)/menthol cooperative catalysis.

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