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Synlett 2006(9): 1410-1412
DOI: 10.1055/s-2006-939709
DOI: 10.1055/s-2006-939709
LETTER
© Georg Thieme Verlag Stuttgart · New York
Ag(I)-Catalyzed Michael Additions of β-Ketoesters to Nitroalkenes in Water: Remarkable Effect of Water as a Reaction Medium on Reaction Rates
Further Information
Received
4 February 2006
Publication Date:
26 April 2006 (online)
Publication History
Publication Date:
26 April 2006 (online)
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Abstract
AgOTf-PPh3 complex-catalyzed Michael additions of β-ketoesters to nitroalkenes in water were performed. The system promotes the reaction efficiently only in water, and interestingly the reaction does not proceed well in organic solvents. In addition, this reaction system could be applied to catalytic asymmetric synthesis in water.
Key words
water - silver - Michael additions - solvent effects - asymmetric synthesis
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References and Notes
The appearance of organic materials in the reaction mixture (solid, liquid, droplets, etc.) depends on the substrate species.
11Various Ag/(R)-Tol-BINAP ratios were tested, and the ratio in Scheme [1] gave better results.
12Extraction solvents other than CH2Cl2 (ex. EtOAc) can also be used.