The asym. .alpha.-hydroxylation of N,N-diprotected .beta.-amino acid esters I (R1 = Ph, PhCH2, PhCH2OCH2; R2 = H), readily prepd. from the corresponding .alpha.-amino acids, proceeded smoothly at -78 and gave esters I (R2 = HO) in 89-95% yields and with high diastereoselectivity (up to 94% de). In comparison with other asym. .alpha.-hydroxylation procedures this method does not need the use of costly chiral reagents and/or chiral auxiliaries and represents the first example of a procedure affording .beta.-amino-.alpha.-hydroxy acids with full, orthogonal protection.

beta-Amino-alpha-hydroxy esters by asymmetric hydroxylation of homo-beta-amino acid esters

CAPUTO, ROMUALDO;GUARAGNA, ANNALISA;PALUMBO, GIOVANNI;PEDATELLA, SILVANA
2002

Abstract

The asym. .alpha.-hydroxylation of N,N-diprotected .beta.-amino acid esters I (R1 = Ph, PhCH2, PhCH2OCH2; R2 = H), readily prepd. from the corresponding .alpha.-amino acids, proceeded smoothly at -78 and gave esters I (R2 = HO) in 89-95% yields and with high diastereoselectivity (up to 94% de). In comparison with other asym. .alpha.-hydroxylation procedures this method does not need the use of costly chiral reagents and/or chiral auxiliaries and represents the first example of a procedure affording .beta.-amino-.alpha.-hydroxy acids with full, orthogonal protection.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11588/365467
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