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Intramolecular Tandem Isomerization–Mannich Reaction as a New Route Towards Aminocyclopentitols
Author(s) -
Cao Hai Thuong,
Roisnel Thierry,
Grée René
Publication year - 2011
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.201101130
Subject(s) - chemistry , isomerization , tandem , intramolecular force , combinatorial chemistry , mannich reaction , cascade reaction , catalysis , stereoselectivity , stereochemistry , organic chemistry , materials science , composite material
A new efficient synthetic strategy has been developed to prepare aminocyclopentitols. It is based on an iron‐catalyzed tandem isomerization–Mannich reaction and uses chiral N ‐ tert ‐butanesulfinamide as a chiral auxiliary. This methodology has been applied to the enantiocontrolled synthesis of a mannostatin A analogue, as well as isomers of known fucosidase and glycosidase inhibitors.