The Journal of Organic Chemistry

Inverse electron demand Diels-Alder reactions of 3-carbomethoxy-2-pyrones. Controlled introduction of oxygenated aromatics: benzene, phenol, catechol, resorcinol, …

DL Boger, MD Mullican

Index: Boger, Dale B.; Mullican, Michael D. Journal of Organic Chemistry, 1984 , vol. 49, # 21 p. 4033 - 4044

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Citation Number: 61

Abstract

CH~ O''OCH~ CH30 OCH3 lie 3i e Method A: The enolate of 1 was generated with 2.2 equiv of NaH in THF (0.2 M) at 0 to 25" C. Method B: The enolate of 1 was generated with 1.2 equiv of LDA in THF (0.2 M) at-78 to-5" C. Method C: The enolate of 1 was generated with 1.2 equiv of LDA in THF (0.2 M) at-78 to-5" C, and closure to the a-pyrone was effected with acetic anhydride treatment at 100 to 130" C. Method D: equiv of NaH in THF (0.2 M) at 0 to ...

~84%

~85%

~67%

~76%

~75%

~69%

An Efficient Synthesis of Substituted 2H-Pyran-2-one Derivat...

[Demir; Tanyeli; Urkmez-Karaaslan; Sayrac Synthetic Communications, 1991 , vol. 21, # 14 p. 1433 - 1441]