Concepedia

FACILE SYNTHESIS OF 2-METHYLENE-4-BUTYROLACTONES

Junzo Nokami, Takashi Tamaoka, Hideki Ogawa, Shoji Wakabayashi

Chemistry Letters · 1986 · 42 citations · 11 references

DOI

Concepts

Abstract

Abstract 2-Methylene-4-butyrolactones were conveniently synthesized by treatment of an aldehyde with 2-carboethoxyallyl(-ic) bromide and metallic tin (and aluminum) in good yields. Protolichesterinic acid was synthesized by employing the method.

References

11

Allylation of aldehydes and ketones in the presence of water by allylic bromides, metallic tin, and aluminum

Junzo Nokami, Junzo Otera, Takuzo Sudo et al. · Organometallics · 1983 · 159 citations

, , +8

Reformatsky-type reactions in aqueous media. Use ofbronometryl-acrylic acid for the synthesis of α-methylene-γ-butyrolactones.

Henri Mattes, Claude Benezra · Tetrahedron Letters · 1985 · 94 citations

, , +3

1,4‐Diazobicyclo[2.2.2]octane‐catalyzed coupling of aldehydes and activated double bonds. Part 3. A short ans practical synthesis of mikanecic acid (4‐vinyl‐1‐cyclohexene‐1,4‐dicarboxylic acid)

H. M. R. Hoffmann, Jürgen P. Rabe · Helvetica Chimica Acta · 1984 · 84 citations

, , +6

Reaction of .pi.-allylnickel bromide complexes with ketones and aldehydes. Synthesis of .alpha.-methylene-.gamma.-butyrolactones

Louis S. Hegedus, S. Wagner, E. L. Waterman et al. · The Journal of Organic Chemistry · 1975 · 84 citations

, , +5

Facile one-pot synthesis of bromo homoallyl alcohols and 1,3-keto acetates via allyltin intermediates

Tadakatsu Mandai, Junzo Nokami, Toru Yano et al. · The Journal of Organic Chemistry · 1984 · 74 citations

, , +6