Über eine neue Synthese von Citral und verwandten Verbindungen

Saucy, G.; Marbet, R.; Lindlar, H.; Isler, O.

doi:10.1002/hlca.19590420624

Cited by 100 publications

(28 citation statements)

References 9 publications

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“…[5e] Heating 11 a in AcOH in the presence of catalytic amounts of Ag 2 CO 3 [13] furnished exclusively the dienol acetate 23, which formally is the Cope-rearrangement product of the expected allene 22 [14] (Scheme 11). 23 may also arise from 20 by retro-[2+2]-cycloaddition.…”

Section: Resultsmentioning

confidence: 99%

Gold‐ and Copper‐Catalyzed Cycloisomerizations towards the Synthesis of Thujopsanone‐Like Compounds

Fehr

Vuagnoux

Buzás

et al. 2011

Chemistry A European J

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In the search for a new access to thujopsanone related compounds by cycloisomerization reactions of unsaturated propargylic alcohols and acetates, we found several interesting reaction types and demonstrated the complementarity of Au, Pt, and Cu catalysts. Thus, 6-en-1-yn-3-ol 10a underwent clean cyclization/ether formation to 16, in particular using Au catalysts (76-98%) or a newly prepared Cu(I)-triflimidate-catalyst (94%). The corresponding acetate 11 a underwent either the cycloisomerization with concomitant [1,2]-acyl shift (to 12: 78% using AuCl(3)) or an unprecedented rearrangement-cycloaddition leading to 20 (43% using [(tBuXPhos)AuNTf(2)]), a strained fused tricyclic ring system containing a [2.2.0] bicyclic subunit.

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Section: Resultsmentioning

confidence: 99%

Gold‐ and Copper‐Catalyzed Cycloisomerizations towards the Synthesis of Thujopsanone‐Like Compounds

Fehr

Vuagnoux

Buzás

et al. 2011

Chemistry A European J

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“…12 Under standard conditions, product 2d was obtained in 83% yield (eq 5). The E/Z ratio of alkylidene cyclohexenone 2d was the same as products directly derived from 1d using a Rh(I) catalyst (Table 1).…”

Section: Resultsmentioning

confidence: 99%

“…11 The 1,3-acyloxy migration of propargyl esters was initially discovered by Saucy and Marbet in 1959 using a silver catalyst. 12 Other transition metal complexes including copper, platinum and gold have also been found to promote the Saucy-Marbet rearrangement. 13,14 The regioselectivity for 1,2- or 1,3-acyloxy migration of propargyl ester was often dependent on the substrates and catalysts.…”

Section: Introductionmentioning

confidence: 99%

Rhodium-Catalyzed Carbonylation of Cyclopropyl Substituted Propargyl Esters: A Tandem 1,3-Acyloxy Migration [5 + 1] Cycloaddition

Shu

Zhang

et al. 2012

J. Org. Chem.

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We have developed two different types of tandem reactions for the synthesis of highly functionalized cyclohexenones from cyclopropyl substituted propargyl esters. Both reactions were initiated by rhodium-catalyzed Saucy-Marbet 1,3-acyloxy migration. The resulting cyclopropyl substituted allenes derived from acyloxy migration then underwent [5+1] cycloaddition with CO. The acyloxy group not only eased the access to allene intermediates but also provided a handle for further selective functionalizations.

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“…6 The reaction could be scaled up to 100g scale. Some of the allenylic acetate intermediates were isolated and characterized by IR.…”

Section: Historical Discovery Of 13- and 12-acyloxy Migration Ofmentioning

confidence: 99%

Rhodium-catalyzed acyloxy migration of propargylic esters in cycloadditions, inspiration from the recent “gold rush”

et al. 2012

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Transition metal-catalyzed acyloxy migration of propargylic esters offers versatile entries to allene and vinyl carbene intermediates for various fascinating subsequent transformations. Most π-acidic metals (e.g. gold and platinum) are capable of facilitating these acyloxy migration events. However, very few of these processes involve redox chemistry, which are well-known for most other transition metals such as rhodium. The coupling of acyloxy migration of propargylic esters with oxidative addition, migratory insertion, and reductive elimination may lead to ample new opportunities for the design of new reactions. This tutorial review summarizes recent developments in Rh-catalyzed 1,3- and 1,2-acyloxy migration of propargylic esters in a number of cycloaddition reactions. Related Au- and Pt-catalyzed cycloadditions involving acyloxy migration are also discussed.

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Über eine neue Synthese von Citral und verwandten Verbindungen

Cited by 100 publications

References 9 publications

Gold‐ and Copper‐Catalyzed Cycloisomerizations towards the Synthesis of Thujopsanone‐Like Compounds

Gold‐ and Copper‐Catalyzed Cycloisomerizations towards the Synthesis of Thujopsanone‐Like Compounds

Rhodium-Catalyzed Carbonylation of Cyclopropyl Substituted Propargyl Esters: A Tandem 1,3-Acyloxy Migration [5 + 1] Cycloaddition

Rhodium-catalyzed acyloxy migration of propargylic esters in cycloadditions, inspiration from the recent “gold rush”

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