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Unusual Magnesium Chloride Catalyzed Non‐Evans anti ‐Aldol Reactions of an Enolizable L ‐Threose Derivative
Author(s) -
McNulty James,
Nair Jerald J.,
Sliwinski Marcin,
Harrington Laura E.,
Pandey Siyaram
Publication year - 2007
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.200700854
Subject(s) - chemistry , aldol reaction , adduct , derivative (finance) , magnesium , stereoselectivity , catalysis , chloride , organic chemistry , stereochemistry , economics , financial economics
The magnesium chloride catalyzed anti ‐aldol reaction of phenyl acetate derived oxazolidinones proceeds readily with enolizable L ‐threose derivative 8 to provide anti ‐aldol adducts in high yields and with very high diastereoselectivities. The reaction is also efficient with aromatic aldehydes and provides slightly lower diastereoselectivities. This extension allows access to stereochemically defined fragments applicable to the synthesis of alkaloid and phenylpropanoid derivatives.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)