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Tetrahedron Letters

Volumn 25, Issue 52, 1984, Pages 5977-5980

Heteroatom directed β-lithiation of a vinyl ether

(2) McDougal, Patrick G a Rico, Joseph G a

a GEORGIA INSTITUTE OF TECHNOLOGY (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0011754220 PISSN: 00404039 EISSN: None Source Type: Journal
DOI: 10.1016/S0040-4039(01)81737-8 Document Type: Article

Times cited : (18)

References (21)

1
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- Gschwend¹ Rodriguez²

2
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- and references therein.
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- Boeckman¹ Bruza²

3
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- (1979) Tetrahedron Lett. , pp. 67
- Ficini¹ Kahn² Falou³ Touzin⁴

4
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- (1978) J. Org. Chem. , vol.43 , pp. 1595
- Lau¹ Schlosser²

5
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- (1981) J. Org. Chem. , vol.46 , pp. 3741
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6
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- (1982) J. Am. Chem. Soc. , vol.104 , pp. 1777
- Kowalski¹ Fields²

7
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- Wollenberg¹ Albizati² Peries³

8
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- For a recent example, see:
- (1984) Tetrahedron Lett. , vol.25 , pp. 483
- Mills¹ Snieckus²

9
- 84918416900
- 3I, NaH (d) s-BuLi, THF, −78° → 0°.

10
- 33845555248
- For a review of benzamide assisted ortho deprotonations, see:
- (1982) Accts. Chem. Research , vol.15 , pp. 306
- Beak¹ Snieckus²

11
- 0010631244
- Deprotonation of enol ethers where the β-directing effecting of oxygen is of secondary importance are known, see:
- (1968) Tetrahedron Lett. , pp. 937
- Ficini¹ Depezay²

12
- 0017319308
- (1976) J. Am. Chem. Soc. , vol.98 , pp. 2008
- Vlattas¹ Della Vecchia² Lee³

13
- 84918416899
- 3. Flash chromatography (20% ethyl acetate-hexane) yielded 6c (66%) as a crystalline solid (mp 52–53°).

14
- 84918416898
- 1H NMR and mass spectroscopy. High resolution MS and/or microanalysis established molecular composition.

15
- 84918416897
- Lau and Schlosser (ref. 3b) determined that the Z enol ether 1 was stable up to −30°C, while the E isomer spontaneously decomposed to acetylene at −80°C. The thermal stability of our reagent as well as the directing influence of the oxygen are the bases for assigning the Z configuration to the enol ether products (6a-6g).

16
- 77957065172
- The Chemical Constituents of AustralianFlindersiaSpecies. XVI. The Constituents of the Wood ofFlindersia laevicarpaC. T. White & Francis
- (1962) Australian Journal of Chemistry , vol.15 , pp. 819
- Breen¹ Ritchie² Taylor³

17
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- The chemical constituents of AustralianFlindersiaspecies. XXI. An examination of the bark and the leaves ofF. laevicarpa
- (1976) Australian Journal of Chemistry , vol.29 , pp. 2023
- Picker¹ Ritchie² Taylor³

18
- 33845551063
- The selectivity using Wilkinson catalyst was 9:1 in favor of the threo product (10a). Unfortunately this was a sluggish reaction and the yield of product was variable. We have yet to experiment with iridium catalysts where precedent exists for such stereoselective reductions, see:
- (1983) J. Am. Chem. Soc. , vol.105 , pp. 1072
- Stork¹ Kahne²

19
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- (1968) J. Am. Chem. Soc. , vol.90 , pp. 3444
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20
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- NMR Experiments on acetals 34: The conformational equilibrium in trans-6-alkyl-4-methyl- and trans-6-alkyl-4-phenyl-1,3-dioxanes. The conformational free energy of the 4-methyl and 4-phenyl groups in 1,3-dioxanes
- (1973) Recueil des Travaux Chimiques des Pays-Bas , vol.92 , pp. 531
- Anteunis¹ Tavernier² Swaelens³

21
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- (1979) Tetrahedron , vol.35 , pp. 691
- Burkert¹

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