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Synlett 1999; 1999(6): 747-749
DOI: 10.1055/s-1999-2715
DOI: 10.1055/s-1999-2715
letter
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α-Silyl Controlled Asymmetric Michael Additions of Acyclic and Cyclic Ketones to Nitroalkenes
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Publikationsverlauf
Publikationsdatum:
31. Dezember 1999 (online)
![](https://www.thieme-connect.de/media/synlett/199906/lookinside/thumbnails/10.1055-s-1999-2715-1.jpg)
Virtually enantiopure α-t-butyldimethylsilyl ketones (R)-1 and (S)-5 are converted regioselectively to the corresponding trimethylsilyl enol ethers (R)-2 and (S,Z)-6. Subsequent asymmetric Michael addition to nitroalkenes in the presence of SnCl4 affords the 1,4-adducts 3 and 7 in good yields and high diastereo- and enantiomeric excesses. Removal of the t-butyldimethylsilyl group with n-Bu4NF, THF, NH4F/HF lead to the α,β-disubstituted γ-nitro ketones (S,R)-4 (de = 91-92%, ee >98%) and (R,S)-8 (de >96%, ee >98%) in very good overall yields.
asymmetric synthesis - Michael addition - α-silyl ketones - nitroalkenes - nitro ketones