TY - JOUR
T1 - Synthesis of chiral β2,2,3-3-amino-2-hydroxyalkanoates and 3-alkyl-3-hydroxy-β-lactams by double asymmetric induction
AU - Guerrini, Andrea
AU - Varchi, Greta
AU - Daniele, Rizzo
AU - Samorì, Cristian
AU - Battaglia, Arturo
N1 - Copyright:
Copyright 2009 Elsevier B.V., All rights reserved.
PY - 2007/8/13
Y1 - 2007/8/13
N2 - Reactions of chiral (2S)-enolates of dioxolan-4-ones, derived from lactic, mandelic, and phenyllactic acids, with aliphatic (SS)- and (SR)-tert-butylsulfinyl aldimines afforded conformationally restrained C2-disubstituted N,O-orthogonally protected 3-amino-2-hydroxyalkanoates in the form of N-sulfinyl protected 1′-aminodioxolan-4-ones. The product distribution showed that there is significant kinetic selectivity, due to the presence of 'matched' and 'mismatched' components, between the (S)- or (R)-tert-butylsulfinyl aldimines and the (2S)-enolates of the 1,3-dioxolan-4-ones. Selective methoxide-induced removal of the acetal group of the N-sulfinyl-1′-aminodioxolanones yielded the corresponding N-sulfinyl protected methyl alkanoates. In addition, the selective acid-induced removal of the sulfinyl group of the N-sulfinyl-1′-aminodioxolanones provided the corresponding N-unprotected 1′-aminodioxolanones, whose base-induced cyclization afforded the corresponding β-lactams.
AB - Reactions of chiral (2S)-enolates of dioxolan-4-ones, derived from lactic, mandelic, and phenyllactic acids, with aliphatic (SS)- and (SR)-tert-butylsulfinyl aldimines afforded conformationally restrained C2-disubstituted N,O-orthogonally protected 3-amino-2-hydroxyalkanoates in the form of N-sulfinyl protected 1′-aminodioxolan-4-ones. The product distribution showed that there is significant kinetic selectivity, due to the presence of 'matched' and 'mismatched' components, between the (S)- or (R)-tert-butylsulfinyl aldimines and the (2S)-enolates of the 1,3-dioxolan-4-ones. Selective methoxide-induced removal of the acetal group of the N-sulfinyl-1′-aminodioxolanones yielded the corresponding N-sulfinyl protected methyl alkanoates. In addition, the selective acid-induced removal of the sulfinyl group of the N-sulfinyl-1′-aminodioxolanones provided the corresponding N-unprotected 1′-aminodioxolanones, whose base-induced cyclization afforded the corresponding β-lactams.
KW - 3-Hydroxy-β-lactams
KW - Aldimines
KW - Dioxolan-4-ones
KW - Double asymmetric induction
KW - α-Hydroxy-β-amino acids
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U2 - 10.1016/j.tet.2007.05.069
DO - 10.1016/j.tet.2007.05.069
M3 - Article
AN - SCOPUS:34347211695
SN - 0040-4020
VL - 63
SP - 7949
EP - 7969
JO - Tetrahedron
JF - Tetrahedron
IS - 33
ER -