Tetrahedron p. 1821 - 1830 (1993)
Update date:2022-09-26
Topics:
Enders, Dieter
Papadopoulos, Kyriakos
Herdtweck, Eberhardt
A simple and efficient enantioselective synthesis of 2-substituted 4-oxosulfones 5 in 40 - 71 percent overall chemical yield and enantiomeric excesses of 86 -> 97 percent is described.The key is an asymmetric Michael-addition of lithiated methylketone-SAMP-/RAMP-hydrazones 3 to α,β-unsaturated phenylsulfones 2.The absolute configuration is determined by X-ray structure analysis of a crystalline hydrazone Michael adduct (4k) and through chemical correlation by polarimetry.
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