Gold‐Catalyzed Intermolecular Addition of Carbonyl Compounds to 1,6‐Enynes

Schelwies, Mathias; Dempwolff, Adrian L.; Röminger, Frank; Helmchen, Günter

doi:10.1002/anie.200701378

Cited by 111 publications

(47 citation statements)

References 41 publications

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“…Helmchen similarly applied the Ph 3 PAuCl/AgSbF 6 catalyst system to the intermolecular trapping of metallocarbenoid reaction intermediates with carbonyl compounds 100. The substitution patterns on the substrates were crucial to successful trapping; only primary alkenes, such as in substrate 133 , were tolerated, in contrast to those tested in the indole trapping experiments described above (Scheme 22).…”

Section: Cascade Reactions Initiated By Carbon Nucleophiles With πmentioning

confidence: 99%

Ligand Effects in Homogeneous Au Catalysis

2008

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F. Dean Toste received his B.Sc. and M.Sc. degrees in chemistry from the University of Toronto where he worked with Prof. Ian W. J. Still. In 1995, he began his doctoral studies at Stanford University under the direction of Professor Barry M. Trost. Following postdoctoral studies with Professor Robert H. Grubbs at Caltech, he joined the faculty at the University of California, Berkeley, in 2002, and was promoted to Associate Professor in 2006. Current research in his group is aimed towards the design of catalysts and catalytic reactions and the application of these methods to chemical synthesis.

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Section: Cascade Reactions Initiated By Carbon Nucleophiles With πmentioning

confidence: 99%

Ligand Effects in Homogeneous Au Catalysis

2008

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“…14,15 Helmchen and later Echavarren in particular have studied the gold(I) catalyzed reaction of aldehydes with 1,6-enynes. 12–14 DFT studies support addition of aldehydes to an electrophilic allyl carbene intermediate (e.g. Scheme 2, top).…”

Section: Introductionmentioning

confidence: 90%

Gold(i)-catalyzed addition of aldehydes to cyclopropylidene bearing 6-aryl-1,5-enynes

Roselli

Gagné

2016

Org. Biomol. Chem.

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A diastereoselective, gold-catalyzed cascading cycloisomerization of alkylidene cyclopropane bearing 1,5-enynes that terminates in a cyclo-addition of aldehydes has been developed. This diastereoselective reaction provides convergent access to novel polycyclic molecular structures (18 examples), and tolerates a diverse scope of aldehydes. Mechanistic studies reveal that the catalytic cycle rests at a digold off-cycle intermediate, one of which was isolated.

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“…The reaction between 1,6-enynes with a terminal alkene group and carbonyl compounds in the presence of cationic Au(I) complexes was reported [177] [Au] The reaction between 1,6-enynes with a terminal alkene group and carbonyl compounds in the presence of cationic Au(I) complexes was reported [177] [Au]…”

Section: Scheme 42 Regioselectivity In the Domino Alkoxylation/cycloimentioning

confidence: 99%