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Solid-phase synthesis of γ-lactams, γ-lactones and cyclobutane derivatives from common resin-bound intermediates

✍ Scribed by Richard C.D Brown; John Keily; Rehana Karim


Publisher
Elsevier Science
Year
2000
Tongue
French
Weight
171 KB
Volume
41
Category
Article
ISSN
0040-4039

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✦ Synopsis


Resin-bound cyclobutanone iminium salts, prepared on the solid-phase using the [2+2]-keteneiminium olefin cycloaddition reaction, have been transformed into a number of distinct structural classes including γ-lactams, γ-lactones, cyclobutylamines and cyclobutanols.


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Resin-bound N-acylated amino acid aldehydes iv were converted in a single step to a-hydroxy phosphonates vii (Pudovik reaction) and in six-steps to hydroxystatine amides viii, demonstrating the utility of intermediates iv for constructing multiple aspartic acid transition-state isosteres.