Warning: Undefined array key "mm" in /www/wwwroot/www.ai-bt.com/si.php on line 10 Deprecated: trim(): Passing null to parameter #1 ($string) of type string is deprecated in /www/wwwroot/www.ai-bt.com/si.php on line 10 Gold(I)-catalyzed enantioselective hydroamination of N-allenyl carbamates.

Literature DB >> 17595096

Gold(I)-catalyzed enantioselective hydroamination of N-allenyl carbamates.

Zhibin Zhang¹, Christopher F Bender, Ross A Widenhoefer.

Abstract

Treatment of the N-4,5-hexadienyl carbamate 2a with a catalytic 1:2 mixture of [(S)-1]Au2Cl2 [(S)-1 = (S)-3,5-t-Bu-4-MeO-MeOBIPHEP] and AgClO4 in m-xylene at -40 degrees C for 24 h led to isolation of 2-vinylpyrrolidine 3a in 97% yield with 81% ee. Gold(I)-catalyzed enantioselective hydroamination was effective for a number of carbamate groups and tolerated terminal disubstitutution of the allenyl moiety.

Entities: Chemical

Mesh：

Substances：
Carbamates
Gold

Year: 2007 PMID： 17595096 DOI： 10.1021/ol071108n

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

Keyword Cloud
Cited

23 in total

1. The enantioselective intramolecular aminative functionalization of unactivated alkenes, dienes, allenes and alkynes for the synthesis of chiral nitrogen heterocycles.

Authors: Sherry R Chemler
Journal: Org Biomol Chem Date: 2009 Impact factor: 3.876

2. Mild, rhodium-catalyzed intramolecular hydroamination of unactivated terminal and internal alkenes with primary and secondary amines.

Authors: Zhijian Liu; John F Hartwig
Journal: J Am Chem Soc Date: 2008-01-10 Impact factor: 15.419

3. Mechanistic analysis of gold(I)-catalyzed intramolecular allene hydroalkoxylation reveals an off-cycle bis(gold) vinyl species and reversible C-O bond formation.

Authors: Timothy J Brown; Dieter Weber; Michel R Gagné; Ross A Widenhoefer
Journal: J Am Chem Soc Date: 2012-05-29 Impact factor: 15.419

10. 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(I)-catalyzed enantioselective hydroamination of N-allenyl carbamates.

1. The enantioselective intramolecular aminative functionalization of unactivated alkenes, dienes, allenes and alkynes for the synthesis of chiral nitrogen heterocycles.

2. Mild, rhodium-catalyzed intramolecular hydroamination of unactivated terminal and internal alkenes with primary and secondary amines.

3. Mechanistic analysis of gold(I)-catalyzed intramolecular allene hydroalkoxylation reveals an off-cycle bis(gold) vinyl species and reversible C-O bond formation.

4. Asymmetric gold-catalyzed lactonizations in water at room temperature.

5. Gold(I)-Catalyzed Intramolecular Hydroamination of N-Allylic,N'-Aryl Ureas to form Imidazolidin-2-ones.

6. Gold(I)-catalyzed enantioselective intramolecular dehydrative amination of allylic alcohols with carbamates.

7. Gold(I)-catalyzed enantioselective synthesis of pyrazolidines, isoxazolidines, and tetrahydrooxazines.

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

9. Enantioselective thiourea-catalyzed intramolecular cope-type hydroamination.

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