2013
DOI: 10.1002/anie.201209850
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Gold‐Catalyzed Cyclization/Oxidative [3+2] Cycloadditions of 1,5‐Enynes with Nitrosobenzenes without Additional Oxidants

Abstract: Golden control: The title reaction (see scheme) proceeds with high stereocontrol to generate the heterocyclic products in good yield. Experiments to probe the mechanism were performed.

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Cited by 56 publications
(12 citation statements)
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“…In 2013, Liu and co-workers [13] reported ag old-catalyzed cyclization/oxidative[ 3 + +2] cycloaddition reaction of 1,5-enynes (14)w ith aromatic nitroso compounds (15;S cheme 6). For (Z)-A,t he initially formed cyclopropylc arbene (B)h ad an alkenylÀ gold carbocation resonance structure (B').…”
Section: Metal-catalyzed Reactions Of Nitroso Compoundsmentioning
confidence: 99%
“…In 2013, Liu and co-workers [13] reported ag old-catalyzed cyclization/oxidative[ 3 + +2] cycloaddition reaction of 1,5-enynes (14)w ith aromatic nitroso compounds (15;S cheme 6). For (Z)-A,t he initially formed cyclopropylc arbene (B)h ad an alkenylÀ gold carbocation resonance structure (B').…”
Section: Metal-catalyzed Reactions Of Nitroso Compoundsmentioning
confidence: 99%
“…Based also in the skeletal rearrangement of enynes, a sequence of cycloisomerisation/cycloaddition was developed by Liu et al These authors explored the reaction of 1,6-enynes using nitrones as a coupling partner (a, Scheme 71) [219] and of 1,5-enynes with nitrosobenzene derivatives (b, Scheme 71) [220]. In the reaction of 1,6-enynes 266, 1,2-oxazepanes 267 were obtained diastereoselectively.…”
Section: Special Cases Of Gold-catalysed Rearrangement Of Enynesmentioning
confidence: 99%
“…Gold catalysts can implement the cycloisomerizations of 1, n ‐enynes ( n =5, 6) through gold carbene intermediates;11 these carbenes implement the cycloadditions of 1,n‐enynes with carbonyl,9 nitrosoarenes,10a or nitrones 10b. With CN‐derived 1,6‐enynes 7 b and 7 b′ as efficient substrates, the intermediacy of gold carbenes can be excluded because no cycloisomerization occurs with the gold catalyst.…”
Section: Reactions Over Various Gold Catalystsmentioning
confidence: 99%