Diastereoselective synthesis of unsaturated vicinal amino alcohols via Diels-Alder reactions of N-sulfinyl dienophiles

RS Garigipati, AJ Freyer, RR Whittle…

Index: Garigipati,R.S.; Freyer,A.J.; Whittle,R.R. Journal of the American Chemical Society, 1984 , vol. 106, p. 7861

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Citation Number: 61

Abstract

Abstract: A novel diastereoselective route for the synthesis of a-hydroxy-8, y-unsaturated amine derivatives is described. The protocol starts with a 3, 6-dihydrothiazine 1-oxide, which is obtained stereoselectively by a Diels-Alder [4+ 21 cycloaddition of a N-sulfinyl dienophile and a 1, 3-diene of known geometry. Fission of the SN bond of the adduct with a Grignard reagent leads to an allylic sulfoxide which is converted stereoselectively to an allyl alcohol ...