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Stereoselective Construction of 2,8‐Dioxabicyclo[3.3.1]nonane/nonene Systems from 3‐ C ‐Branched Glycals
Author(s) -
Reddy Gadi Madhusudhan,
Sridhar Perali Ramu
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.201301665
Subject(s) - nonane , chemistry , stereoselectivity , claisen rearrangement , stereochemistry , organic chemistry , catalysis
A stereoselective approach for the formation of 2,8‐dioxabicyclo[3.3.1]nonane/nonene frameworks through the formation of 3‐ C ‐branched glycals encompassing the Claisen rearrangement of the carbohydrate‐derived allyl‐vinyl ethers and TMSOTf‐catalyzed acetalization reactions as key steps is revealed. A novel acetalization of 3‐ C ‐branched glycals with a tentative mechanism is proposed. The expedient protocol is evaluated by synthesizing a number of 2,8‐dioxabicyclo[3.3.1]nonane/nonene architectures.