Chemistry of carbanions. XV. Stereochemistry of alkylation of 4-tert-butylcyclohexanone

House, Herbert O.; Tefertiller, Ben A.; Olmstead, Hugh D.

doi:10.1021/jo01267a002

Cited by 65 publications

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“…The stereochemistry of alkylations of extended dienolates of enones such as (70) has been extensively investigated (Scheme 33)}41,143 In general, the results are similar to those found for the related decalone enolates (43a) and (44), i.e. steric factors within the anion playa dominant role.…”

Section: Alkylations Of Metal Enolates Of Saturated Aldehydesmentioning

confidence: 70%

Alkylations of Enols and Enolates

Caine

1991

Comprehensive Organic Synthesis

100

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Section: Alkylations Of Metal Enolates Of Saturated Aldehydesmentioning

confidence: 70%

Alkylations of Enols and Enolates

Caine

1991

Comprehensive Organic Synthesis

100

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“…House et ul. have offered a plausible accounting for the weak selectivity in the electrophilic substitution of enolates of cyclohexanones (14).…”

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confidence: 99%

Highly stereoselective H–D exchange of diastereotopic protons in 4′,1″-dimethyl-1,2,3,4-dibenzylcyclohepta-1,3-diene-6-one

Fraser¹,

Champagne²

1976

Can. J. Chem.

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“…27 (2)f 29 (>98)" 29 (>98)' a I n procedure A, the ketone was treated with a mixture of EtoN and MeaSiCl. ref 5f).…”

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confidence: 99%

Chemistry of carbanions. XVIII. Preparation of trimethylsilyl enol ethers

House¹,

Czuba²,

Gall³

et al. 1969

J. Org. Chem.

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808

223

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Two procedures for the preparation of trimethylsilyl enol ethers from aldehydes and ketones are described. Reaction of the ketone with chlorotrimethylsilane and triethylamine in dimethylformamide solution usually affords an equilibrium mixture of the trimethylsilyl enol ethers. Successive reaction of the ketone with lithium diisopropylamide and with chlorotrimethyhilane in l12-dimethoxyethane solution normally produces a mixture in which the less highly substituted enol ether (from kinetically controlled enolate formation) is the principal product. A number of representative structurally and stereochemically isomeric trimethylsilyl enol ethers have been characterized (see Table 11) and their physical properties have been studied. (1968). (5) For descriptions of the preparation of silyl enol ethers, see (a) C. R. Krager and E. G . Rochow, J . Orwnometal. Chem., 1, 476 (1964); (b) J. I. Baukov, G . S. Burlachenko, and I. F. Lutsenko, ibid., 8, 478 (1965); (c) R. J. Fessenden and J. S. Feesenden, J . Ow. Chem., 82, 3535 (1967); (d) R. Bourhis and E. Frainnet, Bull. Soe. Chim. Fr., 3552 (1967); (e) U. Schmidt and M . Schwochan, Tetrahedron Lett., 4491 (1967); (f) G. Stork and P. F. Hudrlik, J . Amer. Chem. Soc., 90, 4462, 4464 (1968). (6) For examples of the rearrangement of 2-silyl ketones to enol ethers, see (a) A. G . Brook, D . M. MacRae, and W. W.Limburg, J . Amer. Chem. Soc., 89, 5493 (1967); (b) I. F. Lutsenko, Yu. I. Baukov, 0. V. Dudukina, and E. N. Kramarova, J . Organometal. Chem., 11, 35 (1968). (8) The use of trimethylsilyl chloride as a scavenger for alkoxides has been used to advantage in the acyloin condensation. See (a) J. J. Bloomfield, Tetrahedron Lett., 587, 591 (1968); (b) G. E. Gream and 9. Worthley, ibid., 3318 (1868).

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Chemistry of carbanions. XV. Stereochemistry of alkylation of 4-tert-butylcyclohexanone

Cited by 65 publications

References 0 publications

Alkylations of Enols and Enolates

Alkylations of Enols and Enolates

Highly stereoselective H–D exchange of diastereotopic protons in 4′,1″-dimethyl-1,2,3,4-dibenzylcyclohepta-1,3-diene-6-one

Chemistry of carbanions. XVIII. Preparation of trimethylsilyl enol ethers

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