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Direct Catalytic Asymmetric Enolexo Aldolizations
Author(s) -
Pidathala Chandrakala,
Hoang Linh,
Vignola Nicola,
List Benjamin
Publication year - 2003
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.200351266
Subject(s) - aldol reaction , catalysis , intramolecular force , cyclohexanes , chemistry , proline , stereochemistry , organic chemistry , amino acid , biochemistry
32 years after the first, and still the only, catalytic asymmetric intramolecular aldol reaction was published in this journal, the proline‐catalyzed Hajos–Parrish–Eder–Sauer–Wiechert reaction is extended for the first time to catalytic asymmetric enolexo aldolizations. The process provides substituted cyclohexanes in excellent diastereo‐ and enantioselectivities. For example, heptanedial is converted into the corresponding cyclic anti ‐configured aldol in 99 % ee (see scheme).