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Synfacts 2005(0): 0058-0058
DOI: 10.1055/s-2005-869918
DOI: 10.1055/s-2005-869918
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York
Direct Dinuclear Zinc Aldol Addition
Contributor(s): Hisashi Yamamoto, Matthew BoxerB. M. Trost*, M. U. Frederiksen, J. P. N. Papillon, P. E. Harrington, S. Shin, B. T. Shireman
Stanford University, USA
Dinuclear Asymmetric Zn Aldol Additions: Formal Asymmetric Synthesis of Fostriecin
J. Am. Chem. Soc. 2005, 127: 3666-3667
Stanford University, USA
Dinuclear Asymmetric Zn Aldol Additions: Formal Asymmetric Synthesis of Fostriecin
J. Am. Chem. Soc. 2005, 127: 3666-3667
Further Information
Publication History
Publication Date:
20 July 2005 (online)
Key words
direct aldol addition - dinuclear zinc - formal synthesis
Significance
This paper utilizes the author’s previously reported direct aldol addition in the formal asymmetric syntheses of fostriecin. The use of alkynyl methyl ketones as an enolate precursor was recently reported by this group and has now been used in the studies of natural product synthesis.
Comment
The dinuclear Zn catalyst has been shown as an excellent catalyst for one of the most interesting transformations, the direct aldol condensation. This catalyst is able to give perfect enantioselectivity. The authors also exemplify the utility of the Pd-catalyzed vinyl silane cross-coupling during the formal synthesis.