Conjugate additions of E-alkenylphosphonates to lithiated Schöllkopf's bislactim ether: Stereocontrolled access to anti 2-amino-3-substituted-4-phosphonobutanoic acids
1996; Elsevier BV; Volume: 37; Issue: 32 Linguagem: Inglês
10.1016/0040-4039(96)01230-0
ISSN1873-3581
AutoresVicente Ojea, Ma Carmen Fernández, Marı́a Ruiz, JoséMa Quintela,
Tópico(s)Synthetic Organic Chemistry Methods
ResumoHighly face-selective Michael addition of lithiated Schöllkopf's bislactim ether (derived from cyclo-[L-val-glyl] 7) to E-alkenylphosphonates 2a-d and 1,3-butadienylphosphonate 2e allows a direct and stereocontrolled access to the excitatory amino acid analogues 2,3-anti-2-amino-3-substituted-4-phosphonobutanoic acids 14a-d and 2-amino-6-phosphono-4-hexenoic acid 15. The relative stereochemistry was assigned from a NMR study of cyclic derivatives 16, 17 and 19.
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