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Asymmetric Michael Addition of Chiral Lithiated Sulfonates to Nitroalkenes: Diastereo- and Enantioselective Synthesis of α,β-Disubstituted γ-Nitro and β-Alkoxycarbonyl Methyl Sulfonates.

✍ Scribed by Dieter Enders; Otto Mathias Berner; Nicola Vignola; Wacharee Harnying

Publisher
John Wiley and Sons
Year
2003
Weight
205 KB
Volume
34
Category
Article
ISSN
0931-7597

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The aza-Michael addition of enantiopure 1-aminopyrrolidines to (E)-alkenyl sulfones in the presence of a catalytic amount of ytterbium trifluoromethanesulfonate [Yb(OTf) 3 ] yields β-hydrazino sulfones in moderate to good yields and with diastereoselectivities of up to 98%. The latter undergo reduct