Facile and Efficient Preparation of Alkyl 6-Oxo-1-cyclohexenecarboxylates

Kato, Masayuki; Kamat, Vijayendra P.; Yoshikoshi, Akira

doi:10.1055/s-1988-27675

Cited by 21 publications

(9 citation statements)

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“…Trimethylaluminum, triethylaluminum, 2-cyclohexen-1-one, 4,4-dimethyl-2-cyclohexen-1-one, and all boron-containing Lewis acids were purchased from Aldrich Chemicals and used as received. (3 E )-1,3-Pentadien-2-yl(pyridine)bis(dimethylglyoximato)cobalt(III) ( 8b ), 1b,e (3 E )-1,3-pentadien-2-yl[4‘-(dimethylamino)pyridine]bis(dimethylglyoximato)cobalt(III) ( 8a ), 1b,e 6-oxo-1-cyclohexene-1-carboxylic acid ethyl ester ( 18 ), and 6-oxo-1-cyclohexene-1-carboxylic acid tert -butyl ester ( 23 ) were prepared according to previously described methods. 3,5,5-Trimethyl-6-oxo-1-cyclohexene-1-carboxylic acid ethyl ester ( 29 ) was prepared via a modification of a previously reported method as described below.…”

Section: Methodsmentioning

confidence: 99%

Transition-Metal-Mediated Exo-Selective Diels−Alder Reactions for the Preparation of Octalones with Unusual Stereochemistries. Reactions of 2-Cobaloxime-Substituted 1,3-Dienes with Cyclohexenones in Thermal and Lewis Acid-Catalyzed [4 + 2] Cycloadditions

and

Welker

1997

J. Org. Chem.

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2-Cobaloxime−(E)-1,3-pentadienyl complexes (cobaloxime = pyridine(dimethylglyoxime)2cobalt(III)) react with a variety of cyclohexenones in [4 + 2] cycloaddition reactions. These cycloaddition reactions produce octalones with cis ring junctions through exo transition states. The octalones are removed from the cobalt via demetalation reactions that replace the cobalt with a hydrogen and provide pyr(dmg)2CoMe, which can be recycled into the synthesis of the starting dienyl complex.

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Section: Methodsmentioning

confidence: 99%

Transition-Metal-Mediated Exo-Selective Diels−Alder Reactions for the Preparation of Octalones with Unusual Stereochemistries. Reactions of 2-Cobaloxime-Substituted 1,3-Dienes with Cyclohexenones in Thermal and Lewis Acid-Catalyzed [4 + 2] Cycloadditions

and

Welker

1997

J. Org. Chem.

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“…Crystal structure of 22b 1-cyclohexenecarboxylate was not formed as expected from the reaction of 20 in acetic acid. [31] The hexahydrobenzofuIrradiation of the chiral dioxinones were carried out unran derivative 21 was the only isolated product. Thus, the der the same conditions as for the achiral ones.…”

Section: Intramolecular Additionmentioning

confidence: 99%

Diastereoselective Addition of Radicals to Chiral 1,3-Dioxin-4-ones

et al. 1999

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Intermolecular addition of radicals to the 1,3‐dioxin‐4‐ones 1a,b and 2a,b with (–)‐menthone incorporated as chiral auxiliary in 2‐position were investigated. Photochemically generated radicals from 1,3‐dioxolane, oxolane, and 2‐propanol were added with high facial selectivity from the more exposed a‐side. Intramolecular addition of 1,3‐dioxolan‐2‐yl radicals to chiral dioxinones proceeded less efficiently and with lower selectivity also from the a‐side. Nevertheless, it was possible to form the new spirocyclic compounds 22–27. The 1,3‐dioxin‐4‐ones 32a,b possessing an unsaturated side chain were attacked by radicals at the terminal double bond. In the case of irradiation of 32b in 1,3‐dioxolane a cyclization followed the intermolecular addition of a 1,3‐dioxolan‐2‐yl radical and the dispiro compound 36 was formed. However, the formation of dispiro compound 40 required two reaction steps starting with irradiation of 32b and bromotrichloromethane. The achiral 1,3‐dioxin‐4‐one 44 possessing an unsaturated side chain at C‐2 was attacked by 1,3‐dioxolan‐2‐yl radicals preferentially at C‐6.

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“…ment with ethylene glycol and acid the resulting acetal-glycidyl ester was transesterified with sodium methoxide in methanol to give compound 65 (21). Then, in two steps, the methyl ester was transformed into P-keto ester 66 (22), which was then treated with aqueous acetic acid to give the desired compound 56 (23). The cycloaddition can also be carried out on 4,4-disubstituted cyclohexenones.…”

Section: Cycloadditions With Substituted Nazarov Reagents P-keto Estersmentioning

confidence: 99%

Stereoselective synthesis of cis-decalins via Diels–Alder and double Michael addition of substituted Nazarov reagents

Lavallée¹,

Spino²,

Ruel³

et al. 1992

Can. J. Chem.

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The base-catalyzed cycloaddition and double Michael cyclization of substituted Nazarov reagents and of l-phenylsulfinyl analogs, with 2-carbomethoxy-2-cyclohexen-I-one 1 yielding cis-decalins is reported. The reaction is highly stereoselective affording cis,cis-or cis,trarls-decalins. Mechanistic aspects are briefly discussed. On dCcrit la cycloaddition catalysCe par des bases des rCactifs de Nazarov substituks, ainsi que d'un analogue 1-phCnylsulfinylC, avec la 2-carbomCthoxy-2-cyclohexenone 1 produisant des cis-dCcalines. La rkaction est hautement stCrCosClective generant des cis,cis-ou cis,trarzs-dCcalines. Les mkcanisrnes de ces reactions sont brikvement discutes. JEAN-FRANCOIS L

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Facile and Efficient Preparation of Alkyl 6-Oxo-1-cyclohexenecarboxylates

Cited by 21 publications

References 0 publications

Transition-Metal-Mediated Exo-Selective Diels−Alder Reactions for the Preparation of Octalones with Unusual Stereochemistries. Reactions of 2-Cobaloxime-Substituted 1,3-Dienes with Cyclohexenones in Thermal and Lewis Acid-Catalyzed [4 + 2] Cycloadditions

Transition-Metal-Mediated Exo-Selective Diels−Alder Reactions for the Preparation of Octalones with Unusual Stereochemistries. Reactions of 2-Cobaloxime-Substituted 1,3-Dienes with Cyclohexenones in Thermal and Lewis Acid-Catalyzed [4 + 2] Cycloadditions

Diastereoselective Addition of Radicals to Chiral 1,3-Dioxin-4-ones

Stereoselective synthesis of cis-decalins via Diels–Alder and double Michael addition of substituted Nazarov reagents

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