IRIS publication 43339467
Stereocontrol in the intramolecular Buchner reaction of diazoketones
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TY - JOUR - Maguire, AR,Buckley, NR,O'Leary, P,Ferguson, G - 1998 - July - Rna-A Publication of The Rna Society - Stereocontrol in the intramolecular Buchner reaction of diazoketones - Validated - () - ARYL DIAZOKETONES RHODIUM(II)-CATALYZED DECOMPOSITION DIAZOMETHYL KETONES EFFICIENT SYNTHESIS DIAZO KETONES CYCLOHEPTATRIENE ALPHA NORCARADIENE CYCLOADDITION CYCLIZATION - 4077 - 4091 - Rhodium(II) acetate catalysed intramolecular Buchner cyclisation of a series of diazoketones 1 proceeds with excellent diastereoselectivity to produce the trans substituted azulenones 2, which exist as a rapidly equilibrating cycloheptatriene-norcaradiene system, from which the norcaradiene tautomers can be efficiently trapped as PTAD cycloadducts 4. The cyclisation-cycloaddition 1 sequence can be conducted in either a stepwise or a tandem process leading to the pentacyclic systems 4 as a single diastereomer in each case. In the reaction of diazoketone If intramolecular cyclopropanation competes with cyclisation to the aromatic ring. DA - 1998/07 ER -
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@article{V43339467, = {Maguire, AR and Buckley, NR and O'Leary, P and Ferguson, G }, = {1998}, = {July}, = {Rna-A Publication of The Rna Society}, = {Stereocontrol in the intramolecular Buchner reaction of diazoketones}, = {Validated}, = {()}, = {ARYL DIAZOKETONES RHODIUM(II)-CATALYZED DECOMPOSITION DIAZOMETHYL KETONES EFFICIENT SYNTHESIS DIAZO KETONES CYCLOHEPTATRIENE ALPHA NORCARADIENE CYCLOADDITION CYCLIZATION}, pages = {4077--4091}, = {{Rhodium(II) acetate catalysed intramolecular Buchner cyclisation of a series of diazoketones 1 proceeds with excellent diastereoselectivity to produce the trans substituted azulenones 2, which exist as a rapidly equilibrating cycloheptatriene-norcaradiene system, from which the norcaradiene tautomers can be efficiently trapped as PTAD cycloadducts 4. The cyclisation-cycloaddition 1 sequence can be conducted in either a stepwise or a tandem process leading to the pentacyclic systems 4 as a single diastereomer in each case. In the reaction of diazoketone If intramolecular cyclopropanation competes with cyclisation to the aromatic ring.}}, source = {IRIS} }
Data as stored in IRIS
AUTHORS | Maguire, AR,Buckley, NR,O'Leary, P,Ferguson, G | ||
YEAR | 1998 | ||
MONTH | July | ||
JOURNAL_CODE | Rna-A Publication of The Rna Society | ||
TITLE | Stereocontrol in the intramolecular Buchner reaction of diazoketones | ||
STATUS | Validated | ||
TIMES_CITED | () | ||
SEARCH_KEYWORD | ARYL DIAZOKETONES RHODIUM(II)-CATALYZED DECOMPOSITION DIAZOMETHYL KETONES EFFICIENT SYNTHESIS DIAZO KETONES CYCLOHEPTATRIENE ALPHA NORCARADIENE CYCLOADDITION CYCLIZATION | ||
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START_PAGE | 4077 | ||
END_PAGE | 4091 | ||
ABSTRACT | Rhodium(II) acetate catalysed intramolecular Buchner cyclisation of a series of diazoketones 1 proceeds with excellent diastereoselectivity to produce the trans substituted azulenones 2, which exist as a rapidly equilibrating cycloheptatriene-norcaradiene system, from which the norcaradiene tautomers can be efficiently trapped as PTAD cycloadducts 4. The cyclisation-cycloaddition 1 sequence can be conducted in either a stepwise or a tandem process leading to the pentacyclic systems 4 as a single diastereomer in each case. In the reaction of diazoketone If intramolecular cyclopropanation competes with cyclisation to the aromatic ring. | ||
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