Creating Chemical Diversity in Indole Compounds by Merging Au and Ru Catalysis

Bandini, Marco; Eichholzer, Astrid; Gualandi, Andrea; Quinto, Tommaso; Savoia, Diego

doi:10.1002/cctc.201000077

Cited by 33 publications

(7 citation statements)

References 92 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…15 Concurrent with our efforts, Bandini and Aponick have developed effective gold(I)-catalyzed methods for the intramolecular arylation 16 and alkoxylation 17 of allylic alcohols, and these results pointed to the feasibility of gold(I)-catalyzed intramolecular allylic amination. Furthermore, Aponick’s demonstration of gold(I)-catalyzed intramolecular amination of propargylic alcohols with secondary alkylamines suggested that alkylamines might also be suitable nucleophiles for gold(I)-catalyzed intramolecular allylic amination.…”

mentioning

confidence: 79%

Gold(I)-Catalyzed Intramolecular Amination of Allylic Alcohols With Alkylamines

Mukherjee

Widenhoefer

2011

Org. Lett.

View full text Add to dashboard Cite

A 1:1 mixture of (1)AuCl [1 = P(t-Bu)2o-biphenyl] and AgSbF6 catalyzes the intramolecular amination of allylic alcohols with alkylamines to form substituted pyrrolidine and piperidine derivatives. Gold(I)-catalyzed cyclization of (R,Z)-8-(N-benzylamino)-3-octen-2-ol (96% ee, 95% de) led to isolation of (R,E)-1-benzyl-2-(1-propenyl)piperidine in 99% yield with 96% ee, consistent with the net syn addition of the amine relative to the departing hydroxyl group.

show abstract

mentioning

confidence: 79%

Gold(I)-Catalyzed Intramolecular Amination of Allylic Alcohols With Alkylamines

Mukherjee

Widenhoefer

2011

Org. Lett.

View full text Add to dashboard Cite

show abstract

“…45 Diastereomerically pure tetrahydro-b-carbolines (THBCs) were also accessible through this methodology starting from enantiomerically pure indolyl-alcohols 54. 46 Moreover, by merging gold(I) catalysis and ruthenium mediated ring-closing processes, the 9-aza-[3.2.2]nona-2,6-diene bicyclic framework 57 was isolated in 47% yield (Scheme 16b).…”

Section: Unactivated Alkenesmentioning

confidence: 99%

Gold-catalyzed decorations of arenes and heteroarenes with C–C multiple bonds

Bandini

2011

Chem. Soc. Rev.

Self Cite

426

View full text Add to dashboard Cite

Synthetic organic chemistry has been markedly affected by the booming of gold catalysis over the past decade. The renaissance of this coinage metal allowed unprecedented transformations to be realized in a highly selective manner and rendered "old chemistry" more accessible from a practical point of view. Particularly, organic compounds containing C-C multiple bonds benefited from the high carbophilicity of gold species, that opened access to a great chemical diversity through direct and selective π-electrophilic activations. Nowadays, the complexity of naturally occurring compounds based on functionalized aromatic frameworks continues to inspire and influence developments in synthetic chemistry. Furthermore, the ubiquitous presence of arene-based systems in pharmaceuticals, agrochemicals, and functional organic materials warrants the growing demand for mild, selective and sustainable synthetic routes to their preparation. In this context, although the peculiar aptitude of gold salts/complexes for interaction with aromatic compounds (auration process) has long been known, the direct catalytic gold decoration of arenes, has risen to prominence only recently. Here, the extensive use of electrophilic activation of C-C multiple bonds by gold species deserves a prominent mention, and the great strides made in the field over the last few years are described in this tutorial review.

show abstract

“…Gold-catalyzed allylic functionalization has been the object of diverse cyclization reactions and has been found to be efficient for the preparation of γ-butyrolactone [90][91][92]. Chen and colleagues examined the Au-catalyzed lactonization of allylic acetate 29 to construct a butyrolactone system ( Figure 11 Bandini and colleagues reported the direct activation of free allylic alcohol 32 by applying a gold catalyst with N-heterocyclic carbene ( Figure 12) [94].…”

Section: Au-catalyzed Oxaallylationmentioning

confidence: 99%

“…Gold-catalyzed allylic functionalization has been the object of diverse cyclization reactions and has been found to be efficient for the preparation of γ-butyrolactone [90][91][92].…”

Section: Au-catalyzed Oxaallylationmentioning

confidence: 99%

A Review of the Pharmacological Activities and Recent Synthetic Advances of γ-Butyrolactones

Hur

Jang

Sim

2021

IJMS

View full text Add to dashboard Cite

γ-Butyrolactone, a five-membered lactone moiety, is one of the privileged structures of diverse natural products and biologically active small molecules. Because of their broad spectrum of biological and pharmacological activities, synthetic methods for γ-butyrolactones have received significant attention from synthetic and medicinal chemists for decades. Recently, new developments and improvements in traditional methods have been reported by considering synthetic efficiency, feasibility, and green chemistry. In this review, the pharmacological activities of natural and synthetic γ-butyrolactones are described, including their structures and bioassay methods. Mainly, we summarize recent advances, occurring during the past decade, in the construction of γ-butyrolactone classified based on the bond formation in γ-butyrolactone between (i) C5-O1 bond, (ii) C4-C5 and C2-O1 bonds, (iii) C3-C4 and C2-O1 bonds, (iv) C3-C4 and C5-O1 bonds, (v) C2-C3 and C2-O1 bonds, (vi) C3-C4 bond, and (vii) C2-O1 bond. In addition, the application to the total synthesis of natural products bearing γ-butyrolactone scaffolds is described.

show abstract

Creating Chemical Diversity in Indole Compounds by Merging Au and Ru Catalysis

Cited by 33 publications

References 92 publications

Gold(I)-Catalyzed Intramolecular Amination of Allylic Alcohols With Alkylamines

Gold(I)-Catalyzed Intramolecular Amination of Allylic Alcohols With Alkylamines

Gold-catalyzed decorations of arenes and heteroarenes with C–C multiple bonds

A Review of the Pharmacological Activities and Recent Synthetic Advances of γ-Butyrolactones

Contact Info

Product

Resources

About