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Efficient Pathways to Precursors of Pyrrolidine Azasugar Structures
Author(s) -
Schierle Kerstin,
Vahle Ruth,
Steckhan Eberhard
Publication year - 1998
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/(sici)1099-0690(199803)1998:3<509::aid-ejoc509>3.0.co;2-v
Subject(s) - chemistry , pyrrolidine , intramolecular force , bicyclic molecule , reagent , combinatorial chemistry , stereochemistry , organic chemistry
Hydroxy‐substituted pyrrolidines are important structural elements in azasugars. Effective precursors for such compounds are pyrrolo‐oxazolidinones of type 1 . Short asymmetric syntheses starting from easily available low‐priced precursors are desirable. Two efficient pathways to these structures starting from the 4‐methoxylated oxazolidinones 2 and 3 , easily accessible from the chiral pool, have been successfully developed. These oxazolidinones can be used as amidoalkylation reagents. Via Sakurai reactions and subsequent intramolecular cyclization, the synthesis of bicyclic pyrrolidines is possible in a stereocontrolled way.