TY - JOUR
T1 - Asymmetric synthesis of homochiral differentially protected bis-β-amino acid scaffolds
AU - Bull, Steven D.
AU - Davies, Stephen G.
AU - Roberts, Paul M.
AU - Savory, Edward D.
AU - Smith, Andrew D.
PY - 2002/6/3
Y1 - 2002/6/3
N2 - A strategy for the asymmetric synthesis of homochiral [(R,R)- or (S,S)-], or meso-(R,S) bis-β-amino acid scaffolds, formally resulting from the stepwise conjugate addition of two differentially protected homochiral lithium amides to two α,β-unsaturated esters attached to a central arene, is demonstrated. Further manipulation enables the efficient synthesis of orthogonally protected pseudo-meso or pseudo-C2 symmetric scaffolds via selective N-benzyl or N-allyl deprotection, enabling regio-, stereo- and chemoselective functionalisation.
AB - A strategy for the asymmetric synthesis of homochiral [(R,R)- or (S,S)-], or meso-(R,S) bis-β-amino acid scaffolds, formally resulting from the stepwise conjugate addition of two differentially protected homochiral lithium amides to two α,β-unsaturated esters attached to a central arene, is demonstrated. Further manipulation enables the efficient synthesis of orthogonally protected pseudo-meso or pseudo-C2 symmetric scaffolds via selective N-benzyl or N-allyl deprotection, enabling regio-, stereo- and chemoselective functionalisation.
KW - Asymmetric synthesis
KW - Conjugate addition
KW - Differential deprotection
KW - Lithium amides
UR - http://www.scopus.com/inward/record.url?scp=0037013920&partnerID=8YFLogxK
U2 - 10.1016/S0040-4020(02)00369-1
DO - 10.1016/S0040-4020(02)00369-1
M3 - Article
AN - SCOPUS:0037013920
SN - 0040-4020
VL - 58
SP - 4629
EP - 4642
JO - Tetrahedron
JF - Tetrahedron
IS - 23
ER -