Gold(<scp>i</scp>) operational in synergistic catalysis for the intermolecular α-addition reaction of aldehydes across allenamides

Ballesteros, Alberto; Morán-Poladura, Pablo; González, José Manuel

doi:10.1039/c5cc09529h

Cited by 32 publications

(16 citation statements)

References 62 publications

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“…Interestingly, two Spanish teams, led by González and by Mascareñas/López, achieved this challenging process almost simultaneously . The reaction conditions were quite similar and highlighted the chemical compatibility and suitability of [Au(IPr)NTf 2 ] (5 or 10 mol‐%) and prolinol silyl ethers 43a and 43b (20 mol‐%) for delivering the final products 42 with moderate to good enantiomeric excesses (Scheme ).…”

Section: Application In Asymmetric Catalysismentioning

confidence: 88%

N‐Allenyl Amides and O‐Allenyl Ethers in Enantioselective Catalysis

Manoni

Bandini

2016

Eur J Org Chem

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Nowadays asymmetric catalysis is an established reality in the organic synthesis community. Nevertheless, the range of applicability both in organic and in organometallic transformations is so large that seeking for new developments seems unstoppable. In this direction, from time to time a new class of "silent" organic compounds rises to prominence and creates new perspectives in the field. Allenyl amides and allenyl A personal dedication: "Asymmetric catalysis represents my personal and primary scientific contact with Prof. Achille Umani-Ronchi. He, together with his ambitious team at the Department of Chemistry 'G. Ciamician' , has contributed substantially in expanding the frontiers of this emerging field since the late 1980s/early 1990s and I took immense advantage of this stimulating environment during my early career in Bologna. The continuing stimulus and encouragement in pursuing unpredictable and non-trivial ultimate goals constitute his 'trademark' as well as personal legacy [

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Section: Application In Asymmetric Catalysismentioning

confidence: 88%

N‐Allenyl Amides and O‐Allenyl Ethers in Enantioselective Catalysis

Manoni

Bandini

2016

Eur J Org Chem

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“…In 2016, González 7 and Mascareñas and López 8 separately adopted a synergistic catalysis to functionalize allenes to construct acyclic quaternary carbon stereocenters. Using a catalytic amount of gold complex and a small molecule catalyst, the addition of the C α –H of aliphatic aldehyde to an allenamide occurred regioselectively at the terminal position of the allene.…”

Section: Acyclic Quaternary Carbon Stereocenters Through Functionaliz...mentioning

confidence: 99%

Acyclic Quaternary Carbon Stereocenters through Transition-Metal-Catalyzed Enantioselective Functionalization of Unsaturated Hydrocarbons

Li¹,

Sun²

2022

Synthesis

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Acyclic quaternary carbon stereocenters occur frequently in natural products, bioactive molecules, and pharmaceutical compounds. Construction of a carbon stereogenic center attached to four different carbons with defined spatial arrangement is a daunting challenge in asymmetric catalysis. Significant efforts have been directed towards the stereoselective construction of such acyclic quaternary carbon stereocenters. In particular, catalytic generation of acyclic quaternary carbon stereocenters through functionalization of unsaturated hydrocarbons is an extremely attractive approach because unsaturated hydrocarbons are easily accessible both in industry and in organic synthesis. In this short review, we summarize the recent advances achieved in this research area, with the aim to inspire future development.1 Introduction2 Acyclic Quaternary Carbon Stereocenters through Functionalization of Allenes3 Acyclic Quaternary Carbon Stereocenters through Functionalization of Dienes4 Acyclic Quaternary Carbon Stereocenters through Functionalization of Mono-alkenes5 Acyclic Quaternary Carbon Stereocenters through Functionalization of Alkynes6 Summary and Outlook

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“…217 In 2016, the use of gold was disclosed simultaneously by the group of González and the group of López in collaboration with Mascareñas for the intermolecular α-functionalization of aldehydes with allenamides catalyzed by gold. 218,219 Both groups used a synergistic gold and organo-catalysis.…”

Section: Umpoled Reaction With Aldehydementioning

confidence: 99%

Metal-Catalyzed Intermolecular Hydrofunctionalization of Allenes: Easy Access to Allylic Structures via the Selective Formation of C–N, C–C, and C–O Bonds

2020

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Gold(i) operational in synergistic catalysis for the intermolecular α-addition reaction of aldehydes across allenamides

Abstract: The intermolecular reaction of allenamides with aldehydes is reported. The designed approach relies on gold(i) and organocatalysis for activating the allenamides and the aldehydes respectively. Conditions to achieve an enantioselective version of this intermolecular reaction are defined.

Cited by 32 publications

References 62 publications

N‐Allenyl Amides and O‐Allenyl Ethers in Enantioselective Catalysis

N‐Allenyl Amides and O‐Allenyl Ethers in Enantioselective Catalysis

Acyclic Quaternary Carbon Stereocenters through Transition-Metal-Catalyzed Enantioselective Functionalization of Unsaturated Hydrocarbons

Metal-Catalyzed Intermolecular Hydrofunctionalization of Allenes: Easy Access to Allylic Structures via the Selective Formation of C–N, C–C, and C–O Bonds

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