Computational and experimental studies on Cu/Au-catalyzed stereoselective synthesis of 1,3-disubstituted allenes
Literature Information
Publication Date
2019-04-16
DOI
10.1039/C9QO00364A
Impact Factor
5.281
Authors
María Magdalena Cid, María Lago-Silva, Marta González Comesaña, Olalla Nieto Faza, Carlos Silva López
View Original
Abstract
Cu- and Au-mediated formation of allenes from terminal alkynes and aldehydes via propargylamine intermediates is hampered by reversibility in the propargylamine formation. The use of a stable Au(I) catalyst in the reaction using a chiral propargylamine provided clues to disentangle the mechanism of the whole process that would have been otherwise hidden. Additionally, the process was observed to be stereoselective when an enantiomerically pure chiral propargylamine was used as starting substrate providing the corresponding 1,3-disubstituted allenes with high enantiomeric ratio.
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
Recommended Compounds
(2R,4R)-1-Boc-4-Aminopyrrolidine-2-carboxylic acid
CAS Number:
132622-98-1
Molecular Formula:
C10H18N2O4
![[4-(Isobutyrylamino)phenyl]boronic acid structure](https://static.chemtradehub.com/structs/874/874219-50-8-6ab5.webp "[4-(Isobutyrylamino)phenyl]boronic acid structure")
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