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Tetrahedron Letters

Volumn 20, Issue 11, 1979, Pages 995-998

Regiospecific α-methylenation and α-methylation of ketones: titanium tetrachloride promoted phenylthiomethylation of silyl enol ethers

(2) Peterson, Ian a Fleming, Ian a

a UNIVERSITY OF CAMBRIDGE (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000961267 PISSN: 00404039 EISSN: None Source Type: Journal
DOI: 10.1016/S0040-4039(01)86072-X Document Type: Article

Times cited : (70)

References (24)

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3
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4
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- Synthesis of Carbocyclic Spiro Compounds via Cycloaddition Routes
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- Krapcho¹

5
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- and references therein.
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- Holy¹ Wang²

6
- 0001046239
- For a direct synthesis of α-methylene ketones by a Mannich route, see
- (1978) Tetrahedron Letters , pp. 2111
- Gras¹

7
- 0002643848
- For a direct synthesis of α-methylene ketones by a Mannich route, see
- (1978) Tetrahedron Letters , pp. 2955
- Gras¹

8
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- Enolate alkylation with bromomethyl sulphides: synthesis of ?-methylene ketones and carboxylic acids
- (1974) Journal of the Chemical Society, Chemical Communications , pp. 135
- Reich¹ Renga²

9
- 85066115648
- O-Silylated Enolates - Versatile Intermediates for Organic Synthesis
- (1977) Synthesis , pp. 91
- Rasmussen¹

10
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- (1969) J. Org. Chem. , vol.34 , pp. 2324
- House¹ Czuba² Gall³ Olsmtead⁴

11
- 0000569691
- Commercially available from Lancaster Synthesis, or by chlorination of thioanisole:
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- Trost¹ Kunz²

12
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13
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14
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15
- 0002500867
- For the alkylation of silyl enol ethers with t-alkyl halides, see
- (1977) Tetrahedron Letters , pp. 4183
- Chan¹ Paterson² Pinsonnault³

16
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- tert-Alkylation of Ketones and Aldehydes
- (1978) Angewandte Chemie International Edition in English , vol.17 , pp. 48
- Reetz¹ Maier²

17
- 84918338535
- See preceding paper.

18
- 84918338534
- 7 was cyclooctanone, which was benzylthiomethylated in only 51% yield.

19
- 84918338533
- In detail, the amount of regioisomer produced was proportional to the amount of the corresponding silyl enol ether present in the starting material. The major regioisomer (20 from 19, 23 from 22, and 27 from 26) was separated from the minor by column chromatography. In the case of 30, chromatography removed only one of the diastereoisomers of 27 and the other (

20
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- Coll.
- (1955) Org. Synth. , vol.3 , pp. 181
- Mozingo¹

21
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22
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24
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- Conia¹ Girard²

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