Tetrahedron Letters p. 4311 - 4314 (1997)
Update date:2022-09-26
Topics:
Ojea, Vicente
Conde, Susana
Ruiz, Maria
Fernandez, Ma Carmen
Quintela, Jose Ma
Face-selective 1,6-addition of lithiated Schollkopf's bislactime ether 5 to 4-substituted, 1,4- or 3,4-disubstituted 1E,3E-butadienylphosphonates 6a-d allows a direct and stereocontrolled access to semi-rigid AP6 analogues, the 2,3-anti-4E 2-amino-6-phosphono-4-hexenoic acid derivatives 4a-c. The relative stereochemistry was assigned from a NMR study of the cyclic derivative 12c. Tenmembered trans-fused chair-boat-like transition states are invoked to rationalize the stereochemical outcome of the addition.
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Doi:10.1080/00397919708004187
(1997)Doi:10.1021/om9703245
(1997)Doi:10.1055/s-1997-5748
(1997)Doi:10.1016/S0960-894X(97)10151-2
(1998)Doi:10.1021/ic970189o
(1997)Doi:10.1039/a806959j
(1998)