Tetrahedron p. 7063 - 7086 (1996)
Update date:2022-07-29
Topics:
Castejon, Patricia
Moyano, Albert
Pericas, Miquel A.
Riera, Antoni
A convenient entry to enantiopure syn or anti β-hydroxy-γ-amino acids is described. The starting compounds for the synthesis, anti 3-amino-1,2-diols, are readily available in high enantiomeric purity through catalytic asymmetric epoxidation of an allylic alcohol and titanium-promoted oxirane opening. After adequate protection of the nitrogen, a stereodivergent sequence leads to both anti and syn N-Boc aminoalkyl epoxides. Subsequent regioselective ring-opening with cyanide, protection of the resulting secondary alcohol and nitrile to carboxyl conversion afford, in good yields, protected β-hydroxy-γ-amino acid belonging to either the anti (erythro) or syn (threo) series. This methodology has been applied to the enantioselective preparation of cyclohexylstatine, a key component of several aspartyl protease inhibitors, in fully protected form.
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Doi:10.1002/cber.19961290619
(1996)Doi:10.1139/v65-213
(1965)Doi:10.1039/c5ra06620d
(2015)Doi:10.1039/DT9960002275
(1996)Doi:10.1016/0040-4020(96)00267-0
(1996)Doi:10.1002/hlca.19960790314
(1996)