Science of Synthesis

Afarinkia, K.; Vinader, V., Science of Synthesis, (2003) 14, 286.

There are a number of examples of addition of active methylene compounds (e.g., ‌29‌) to acrylates bearing a leaving group at the β-position. The most common group at the β-position is an amino group. Addition of enolate anions and the enol form of acetylacetone to ‌22‌ (‌Schemes 22‌ and ‌23‌, ‌Table 4‌) have been reported.[‌82‌,‌83‌] Additions of 1,3-dicarbonyls to acrylates bearing amino groups at the α- and β-positions, e.g. ‌23‌ (‌Scheme 24‌, ‌Table 5‌), is an excellent method for preparation of 3-amido-2H-pyran-2-ones,[‌84‌–‌88‌] although they have also been prepared from ‌24‌[‌89‌] and ‌25‌.[‌90‌] 3-Hydroxy-2H-pyran-2-ones can be prepared in a similar manner.[‌91‌] Other leaving groups employed at the β-position are alkoxy groups, as in ‌26‌[‌30‌,‌92‌,‌93‌] and ‌27‌.[‌94‌–‌97‌] Additions to cyclic analogues such as ‌28‌ have also been reported.[‌98‌–‌100‌]

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‌Meeeee 88‌ Meeeeeeee ee 8,8-Meeeeeeeeee eeee Meeeeee Meeeeeeee[‌88‌,‌88‌]

‌Meeee 8‌ Meeeeeeee ee 8,8-Meeeeeeeeee eeee Meeeeee Meeeeeeee[‌88‌]

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Meeeee-8-eeeeee-8-eeeeee-8-eee-8M-eeeee-8-eeeeeeeeeee (‌88‌, M8 = M8 = Me); Meeeeee Meeeeeeee:[‌88‌]

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References

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• 8.Meeeee-Meee, (8888) 8/8, 888.