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Current progress in the asymmetric aldol addition reaction.
Chem Soc Rev. 2004 Feb 20; 33(2):65-75.CS

Abstract

Control of stereochemistry during aldol addition reactions has attracted considerable interest over the years as the aldol reaction is one of the most fundamental tools for the construction of new carbon-carbon bonds. Several strategies have been implemented whereby eventually any single possible stereoisomeric aldol product can be accessed by choosing the appropriate procedure. With earlier methods, stoichiometric quantities of chiral reagents were required for efficient asymmetric induction, with the auxiliary most often attached covalently to the substrate carbonyl. Lewis acid catalyzed addition reactions of silyl enolates to aldehydes (Mukaiyama reaction) later opened the way for catalytic asymmetric induction. In the last few years, both chiral metal complexes and small chiral organic molecules have been found to catalyse the direct aldol addition of unmodified ketones to aldehydes with relatively high chemical and stereochemical efficiency. These techniques along with the more recent developments in the area are discussed in this tutorial review.

Authors+Show Affiliations

Departamento de Química Orgánica I, Facultad de Química, Universidad del País Vasco, Apdo. 1072, 20080-San Sebastián, Spain. qoppanic@sc.ehu.esNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't
Review

Language

eng

PubMed ID

14767502

Citation

Palomo, Claudio, et al. "Current Progress in the Asymmetric Aldol Addition Reaction." Chemical Society Reviews, vol. 33, no. 2, 2004, pp. 65-75.
Palomo C, Oiarbide M, García JM. Current progress in the asymmetric aldol addition reaction. Chem Soc Rev. 2004;33(2):65-75.
Palomo, C., Oiarbide, M., & García, J. M. (2004). Current progress in the asymmetric aldol addition reaction. Chemical Society Reviews, 33(2), 65-75.
Palomo C, Oiarbide M, García JM. Current Progress in the Asymmetric Aldol Addition Reaction. Chem Soc Rev. 2004 Feb 20;33(2):65-75. PubMed PMID: 14767502.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Current progress in the asymmetric aldol addition reaction. AU - Palomo,Claudio, AU - Oiarbide,Mikel, AU - García,Jesús M, Y1 - 2004/01/20/ PY - 2004/2/10/pubmed PY - 2004/4/20/medline PY - 2004/2/10/entrez SP - 65 EP - 75 JF - Chemical Society reviews JO - Chem Soc Rev VL - 33 IS - 2 N2 - Control of stereochemistry during aldol addition reactions has attracted considerable interest over the years as the aldol reaction is one of the most fundamental tools for the construction of new carbon-carbon bonds. Several strategies have been implemented whereby eventually any single possible stereoisomeric aldol product can be accessed by choosing the appropriate procedure. With earlier methods, stoichiometric quantities of chiral reagents were required for efficient asymmetric induction, with the auxiliary most often attached covalently to the substrate carbonyl. Lewis acid catalyzed addition reactions of silyl enolates to aldehydes (Mukaiyama reaction) later opened the way for catalytic asymmetric induction. In the last few years, both chiral metal complexes and small chiral organic molecules have been found to catalyse the direct aldol addition of unmodified ketones to aldehydes with relatively high chemical and stereochemical efficiency. These techniques along with the more recent developments in the area are discussed in this tutorial review. SN - 0306-0012 UR - https://www.unboundmedicine.com/medline/citation/14767502/Current_progress_in_the_asymmetric_aldol_addition_reaction_ L2 - https://doi.org/10.1039/b202901d DB - PRIME DP - Unbound Medicine ER -