Synthesis of 3-carbomethoxy-3,4-dialkylcyclohexanones

Grootaert, W. M.; Mijngheer, R.; Clercq, Pierre J. De

doi:10.1016/s0040-4039(00)87594-2

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Formation Of Unsaturated Carbocycles: Scope and Methodology1

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1983

2018

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Cited by 9 publications

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“…15% of enone 42 (see Scheme 7). 48 He proposes that enone 42 arises from intramolecular 1,3-hydride transfer in intermediate a-silyl cation 43, although its The related cyclization reactions of vinylsilanes and acetals occurs in better yields and is a key step in a synthesis of unsymmetrical biphenyls (see Scheme 8) developed by Tius.49 Addition of (trimethylsilyl)allyllithium (46)50 to /3-keto acetals 47 perhaps via oxonium ion 49 and /3-silyl cation 50, although the timing of the dehydration and methanol loss was not established. The method is limited in that it cannot be applied to the synthesis of benzoannulated aliphatic ketones.…”

Section: Formation Of Unsaturated Carbocycles: Scope and Methodologymentioning

confidence: 99%

Vinylsilane- and alkynylsilane-terminated cyclization reactions

Blumenkopf¹,

Overman²

1986

Chem. Rev.

333

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Section: Formation Of Unsaturated Carbocycles: Scope and Methodologymentioning

confidence: 99%

Vinylsilane- and alkynylsilane-terminated cyclization reactions

Blumenkopf¹,

Overman²

1986

Chem. Rev.

333

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TheBirch Reduction of Aromatic Compounds

Rabideau

Marcinow²

1992

Organic Reactions

131

138

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The reduction of aromatic compounds by alkali metals in liquid ammonia represents an important method for the preparation of partially unsaturated six‐membered rings. The reaction was discovered by Wooster and Godfrey, but the major development resulted from the efforts of A. J. Birch, and the reaction has since come to bear his name. Although a variety of metals can be used, the most common are sodium and lithium, and, to a lesser extent, potassium. Cosolvents such as ether or tetrahydrofuran (THF) are often used to improve solubility, and weak acids such as alcohols may be employed during the reaction as proton sources. The latter are necessary for the reduction of benzene and its unactivated derivatives. Improvement in experimental procedures by Wilds and Nelson, the application to polynuclear compounds by Hückel and later by Harvey, and the development of methods for the alkylation of the anions generated in this process (i.e., reductive alkylation) have made this reaction an important approach to the synthesis of a wide variety of organic compounds.

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The Total Synthesis of Tri‐ and Tetracyclic Diterpenes

Goldsmith

1991

Total Synthesis of Natural Products

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Synthesis of 3-carbomethoxy-3,4-dialkylcyclohexanones

Cited by 9 publications

References 4 publications

Vinylsilane- and alkynylsilane-terminated cyclization reactions

Vinylsilane- and alkynylsilane-terminated cyclization reactions

TheBirch Reduction of Aromatic Compounds

The Total Synthesis of Tri‐ and Tetracyclic Diterpenes

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