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Synfacts 2008(1): 0056-0056
DOI: 10.1055/s-2007-991488
DOI: 10.1055/s-2007-991488
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York
Preparation of Thiolated Direct Aldol anti-Products
G. Zhou, J. M. Yost, S. J. Sauer, D. M. Coltart*
Duke University, USA
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
18. Dezember 2007 (online)
Significance
A very mild and operationally simple procedure was devised to obtain anti-aldol products 3 in high diastereoselectivity. The reaction obviates the usual need to work under anhydrous conditions or at low temperatures. Noting that anti selectivity is less common in aldol chemistry, the authors conducted a thorough study of the reaction and showed that the stereochemical outcome of 3 is strongly dependent on the nature of the thiolate counterion. They propose that formation of an (E)-O-enolate is favored through coordination of a lithium ion to both sulfur atoms of the molecule.