Enantioselective synthesis of 2,6-dideoxy carbasugars based on a desymmetrizing hydroformylation-carbonyl ene cyclization process.
A practical one-pot process involving a desymmetrizing hydroformylation with the aid of a chiral catalyst-directing group (CDG*), followed by a carbonyl ene cyclization provides a straightforward access to both enantiomers of the resulting cyclohexanediol; further divergent, highly selective and protecting group-free transformations furnish the carbocyclic analogues of four important 2,6-dideoxysugars.
Breit
Bernhard
B
Institut für Organische Chemie und Biochemie, Albert-Ludwigs-Universität Freiburg, Albertstr. 21, 79104 Freiburg, Germany. bernhard.breit@chemie.uni-freiburg.de
Bigot
Aurélien
A
D054329:Carbasugars / Q000138:chemical synthesis*; D003500:Cyclization; D007659:Ketones / Q000737:chemistry*; D013237:Stereoisomerism
D054329:Carbasugars; D007659:Ketones