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Chiral anchor groups for oxoanions: Asymmetric synthesis of tetrasubstituted bicyclic guanidines
Author(s) -
Schmidtchen Franz P.,
Oswald Heike,
Schummer Anita
Publication year - 1991
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.199119910199
Subject(s) - chemistry , bicyclic molecule , guanidine , yield (engineering) , alkylation , ether , enantioselective synthesis , stereochemistry , salt (chemistry) , combinatorial chemistry , organic chemistry , catalysis , materials science , metallurgy
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 C 1 ‐building block to yield the target structure 1 . The diastereoselectivity (%de) and enantioselectivity (%ee) of the synthetic pathway exceed 94%.