Copper‐Catalyzed Enantioselective Three‐Component Synthesis of Optically Active Propargylamines from Aldehydes, Amines, and Aliphatic Alkynes

Nakamura, Shuichi; Ohara, Mutsuyo; Nakamura, Yuko; Shibata, Norio; Toru, Takeshi

doi:10.1002/chem.200903550

Cited by 125 publications

(28 citation statements)

References 45 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…The same year, Benaglia et al studied the enantioselective three-component reaction of phenylacetylene with primary amines and aldehydes catalyzed by copper complexes of BINOL-derived bis-imines, providing moderate enantioselectivities (≤75% ee) [38]. [39]. Their reaction with aromatic and aliphatic aldehydes 47 and p-anisidine 93a afforded, in the presence of a combination of Cu(OTf) 2 with a related chiral C 2 -symmetric Pybox ligand 96, the corresponding chiral amines 95 in low to high yields (28-93%) and good to excellent enantioselectivities (81-98% ee), as shown in Scheme 31.…”

Section: Three-component Domino Reactions Of Alkynes Aldehydes and Amentioning

confidence: 99%

Green Copper Catalysis in Enantioselective Domino Reactions

Pellissier

2019

COC

View full text Add to dashboard Cite

This review collects for the first time enantioselective domino reactions promoted by chiral green copper catalysts, covering the literature since the beginning of 2006. It is divided into two parts dealing successively with asymmetric twocomponent domino reactions and three-component processes. The first part is dedicated to two-component asymmetric domino reactions, including Michael-initiated processes, domino reactions based on cyclizations, domino reactions initiated by aldol-type condensations and Friedel−Crafts-initiated domino processes. The second part collects asymmetric threecomponent processes, such as Michael-initiated domino reactions, domino reactions between alkynes, aldehydes and amines, domino reactions based on 1,3-dipolar cycloadditions among other three-component reactions.

show abstract

Section: Three-component Domino Reactions Of Alkynes Aldehydes and Amentioning

confidence: 99%

Green Copper Catalysis in Enantioselective Domino Reactions

Pellissier

2019

COC

View full text Add to dashboard Cite

show abstract

“…In 2010, Nakamura et al extended the scope of this type of three-component reaction to the use of aliphatic terminal alkynes. [162] The reaction of these alkynes with a range of aldehydes and p-anisidine afforded, in the presence of a catalytic amount of a combination of Cu(OTf) 2 with a closely related chiral C 2symmetric Pybox ligand, the corresponding chiral amines in good yields and remarkable enantioselectivities of up to 98% ee. It must be noted that Benaglia et al have also studied the threecomponent reaction of phenylacetylene with amines and aldehydes upon catalysis by copper complexes of chiral bis-imines.…”

Section: Multicomponent Reactions Of Alkynes Aldehydes and Aminesmentioning

confidence: 99%

Recent Developments in Enantioselective Metal‐Catalyzed Domino Reactions

2012

View full text Add to dashboard Cite

International audienceSince the first definition of domino reactions by Tietze in 1993, an explosive number of these fascinating reactions have been developed, allowing easily building complex chiral molecular architectures from simple materials to be achieved in a single step. Even more interesting, the possibility to join two or more reactions in one asymmetric domino process catalyzed by chiral metal catalysts has rapidly become one challenging goal for chemists, due to economical advantages, such as avoiding costly protecting groups and time-consuming purification procedures after each step. The explosive development of enantioselective metal-catalyzed domino including multicomponent reactions is a consequence of the considerable impact of the advent of asymmetric transition-metal catalysis. This review aims to update the last developments of enantioselective one-, two-and multicomponent domino reactions mediated by chiral metal catalysts, covering the literature since the beginning of 2006

show abstract

“…To date, many transition‐metal catalysts including gold, silver, copper, iridium, nickel, iron, and indium have been employed for the synthesis of propargylamines. The first A 3 coupling of aldehydes, alkynes, and amines catalyzed by gold in water was developed by Wei et al at 2003 .…”

Section: Introductionmentioning

confidence: 99%

Highly Efficient Aqueous Synthesis of Propargylamines through C–H Activation Catalyzed by Magnetic Organosilica‐Supported Gold Nanoparticles as an Artificial Metalloenzyme

et al. 2018

View full text Add to dashboard Cite

Highly efficient magnetic organosilica-supported gold nanoparticles were developed as an artificial metalloenzyme for the synthesis of propargylamines through C-H activation in water under an ambient atmosphere. Herein, we present a very simple and efficient method for the deposition of Au nanoparticles on porous magnetic organosilica (Fe 3 O 4 @SiO 2 -Cl) through the thermal reduction of an organometallic Au III complex. As a nucleophile, a Au III polypyridyl coordination complex could react with alkyl halides from the Fe 3 O 4 @SiO 2 -Cl to form a quaternary ammonium salt as an ionic Scheme 1. Various pathways for the synthesis of propargylamines.[a]

show abstract

Copper‐Catalyzed Enantioselective Three‐Component Synthesis of Optically Active Propargylamines from Aldehydes, Amines, and Aliphatic Alkynes

Cited by 125 publications

References 45 publications

Green Copper Catalysis in Enantioselective Domino Reactions

Green Copper Catalysis in Enantioselective Domino Reactions

Recent Developments in Enantioselective Metal‐Catalyzed Domino Reactions

Highly Efficient Aqueous Synthesis of Propargylamines through C–H Activation Catalyzed by Magnetic Organosilica‐Supported Gold Nanoparticles as an Artificial Metalloenzyme

Contact Info

Product

Resources

About