Jb. Behr et al., A STRAIGHTFORWARD SYNTHESIS OF (PLUS-OR-MINUS)-4-AMINO-4-DEOXYERYTHROSE VIA ITS BISULFITE ANOMER, Heterocycles, 37(2), 1994, pp. 747-750
Hetero-Diels-Alder reaction of N-butadienyl-2-pyrrolidone (1a) with ac
ylnitroso dienophile (3) led with very high regioselectivity to the ra
cemic cycloadduct (6). A sequence of stereospecific reactions, as well
as some protection/deprotection steps, gave the bisulfite derivative
(2b) of (+/-)-4-amino-4-deoxyerythrose (2a) as a single and crystallin
e anomer. Asymmetric induction as applied to the Diels-Alder cycloaddi
tion step with various N-butadienylpyroglutamate esters (1b-e) permitt
ed to work out optimal experimental conditions, the best d.e. value be
ing 76%.