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20.5.9.1.2.2 Variation 2: Formation of α,α-Diamino Esters

DOI: 10.1055/sos-SD-020-01027

Westbrook, J. A.; Schaus, S. E.Science of Synthesis, (2007201119.

When treated with nucleophilic amines or diamines, α-oxo esters are converted into α,α-diamino esters. The majority of the examples of such heterocyclic α,α-diamino esters serve as novel compounds for biological studies or as complex, synthetic intermediates. For example, 2-aminobenzylamine has been used under dehydration conditions to produce the desired N,N-acetal intermediate 8 in high yield (Scheme 4).[‌1‌] An expansion of studies with tert-butyl 2,3-dioxopent-4-enoate (9) includes condensation reactions with β-lactams which results in tricyclic compounds such as 10.[‌14‌] These compounds have a similar structure to carbacephams and carbapenams. A similar strategy can be used to form carbamoyl-substituted dihydropurine derivatives, e.g. 11, in good yield.[‌31‌] The reaction of α-oxo ester 12 to provide the α,α-diamino derivative 13 has been used en route to a synthetic analogue for perturbation of a vitamin K carboxylase (Scheme 4).[‌32‌]

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