TY - JOUR
T1 - Chiral anchor groups for oxoanions
T2 - Asymmetric synthesis of tetrasubstituted bicyclic guanidines
AU - Schmidtchen, Franz P.
AU - Oswald, Heike
AU - Schummer, Anita
PY - 1991
Y1 - 1991
N2 - The asymmetric synthesis of a tetrasubstituted bicyclic guanidine 1 is described. This salt may serve as an oxoanionbinding modul in open‐chain artificial receptors. The synthetic key step involves asymmetric alkylation of a Schöllkopf bislactim ether 8a/b to produce after protection/deprotection steps a chiral open‐chain triamine 13 which can be cyclized by thiophosgene as a C1‐building block to yield the target structure 1. The diastereoselectivity (%de) and enantioselectivity (%ee) of the synthetic pathway exceed 94%.
AB - The asymmetric synthesis of a tetrasubstituted bicyclic guanidine 1 is described. This salt may serve as an oxoanionbinding modul in open‐chain artificial receptors. The synthetic key step involves asymmetric alkylation of a Schöllkopf bislactim ether 8a/b to produce after protection/deprotection steps a chiral open‐chain triamine 13 which can be cyclized by thiophosgene as a C1‐building block to yield the target structure 1. The diastereoselectivity (%de) and enantioselectivity (%ee) of the synthetic pathway exceed 94%.
KW - Amino acid alkylation
KW - Asymmetric synthesis
KW - Guanidinium anchor group
KW - Molecular recognition
KW - Oxoanion host
UR - http://www.scopus.com/inward/record.url?scp=84986680738&partnerID=8YFLogxK
U2 - 10.1002/jlac.199119910199
DO - 10.1002/jlac.199119910199
M3 - Article
AN - SCOPUS:84986680738
SN - 0170-2041
VL - 1991
SP - 539
EP - 543
JO - Liebigs Annalen der Chemie
JF - Liebigs Annalen der Chemie
IS - 6
ER -