Abstract
Under microwave (MW) heating, 1-diethoxyphosphorylbuta-1,3-diene
cycloadds to diethyl, diisopropyl and di-tert -butyl azodicarboxylates
leading to the corresponding hetero Diels-Alder (HD-A)
cycloadducts in excellent yields. Cycloaddition to the di-tert -butyl derivative is conveniently
scaled up using a six-entry parallel synthesis rotor (>10
g scale). B3LYP/6-31G** calculations confirmed
the concerted, but highly asynchronous character of this reaction.
The di-tert -butyloxycarbonyl cycloadduct
is compatible with orthogonal deprotection (i.e., selective N-deprotection
without degradation of the phosphonate ester). Thus, reduction and
dihydroxylation of the C=C bond of this cycloadduct, followed
by TFA deprotection, gave 3-diethoxyphosphorylhexahydro-1,2-pyridazine and
3-diethoxyphosphoryl-4,5-dihydroxyhexahydro-1,2-pyridazine,
respectively. This HD-A strategy offers a convenient entry
towards phosphonate bioisosters of cyclic α-hydrazino acid
and azafagomine derivatives in racemic series.
Key words
azo compounds - cycloadditions - Diels-Alder
reactions - heterocycles - phosphorus
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