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Intramolecular Stereoselective Protonation of Aldehyde‐Derived Enolates
Author(s) -
Kena Diba Anastasie,
Noll Claudia,
Richter Michael,
Gieseler Marc Timo,
Kalesse Markus
Publication year - 2010
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201004619
Subject(s) - protonation , intramolecular force , hemiacetal , epimer , aldehyde , chemistry , conjugate , aldol reaction , stereoselectivity , stereochemistry , computer science , philosophy , information retrieval , organic chemistry , mathematics , catalysis , ion , mathematical analysis
Picking sides : Asymmetric protonation of the titled compounds poses a most significant challenge and has been addressed by taking advantage of internal protonation and subsequent hemiacetal formation to avoid epimerization (see scheme). The substrates employed in these transformations can be easily accessed through a sequence of vinylogous aldol reactions with subsequent conjugate reductions.