Premium
Claisen Rearrangement of Carbohydrate‐Derived Precursors Towards Highly Functionalized Cyclooctenones with L ‐ xylo , D ‐ arabino and L ‐ lyxo Configuration and Their Diastereoselective Transformations
Author(s) -
Jürs Stefan,
Werschkun Barbara,
Thiem Joachim
Publication year - 2006
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.200600455
Subject(s) - chemistry , enantiopure drug , regioselectivity , claisen rearrangement , carbohydrate chemistry , nuclear magnetic resonance spectroscopy , stereochemistry , carbohydrate , organic chemistry , enantioselective synthesis , catalysis
D ‐Glucose and D ‐mannose have been transformed into precursors incorporating allyl vinyl ether substructures. Both thermally and catalytically, these cyclic allyl vinyl ethers could be converted into the corresponding Claisen rearrangement products. The conformations of these enantiopure 5‐cyclooctenones were studied by NMR spectroscopy and X‐ray crystallography. They proved to be versatile substrates for highly stereo‐ and regioselective modifications. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)