Stereoselective Construction of 2,8‐Dioxabicyclo[3.3.1]nonane/nonene Systems from 3‐ C ‐Branched Glycals | Zendy

Reddy Gadi Madhusudhan | Zendy; Sridhar Perali Ramu | Zendy

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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.

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