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Stereoselective Synthesis of β‐Sulfinylamino Isocyanides and 2‐Imidazolines
Author(s) -
Janssen Guido V.,
VicenteGarcía Esther,
Vogel Wouter,
Slootweg J. Chris,
Ruijter Eelco,
Lammertsma Koop,
Orru Romano V. A.
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201402210
Subject(s) - chemistry , stereoselectivity , optically active , isocyanide , combinatorial chemistry , enantioselective synthesis , imidazoline receptor , stereochemistry , organic chemistry , catalysis , medicine
An efficient asymmetric synthesis of β‐sulfinylamino isocyanides is reported on the basis of the highly diastereoselective addition of 9‐isocyanofluorene to optically pure N ‐ tert ‐butanesulfinimines. The resulting optically pure isocyanides readily cyclized to give optically pure 2‐imidazolines upon removal of the sulfinyl group. Furthermore, the β‐sulfinylamino isocyanides were used as chiral inputs in Ugi and Passerini multicomponent reactions to generate new types of (pseudo)peptide scaffolds.