Tetrahedron: Asymmetry

Synthesis of C 2 symmetric primary vicinal diamines. Double stereospecific Mitsunobu reaction on the heterocyclic diols derived from tartaric acid

J Skarżewski, A Gupta

文献索引：Skarzewski, Jacek; Gupta, Anil Tetrahedron Asymmetry, 1997 , vol. 8, # 11 p. 1861 - 1867

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被引用次数: 55

摘要

Homochiral 1-alkyl-3, 4-dihydroxypyrrolidines,(S, S)-and (R, R)-5 were obtained by cyclization and reduction of both enantiomers of (+)-and (−)-tartaric acid, respectively. Also (S, S)-3, 4-dihydroxytetrahydrofurane 6 was prepared from (+)-diethyl tartrate. All these heterocyclic vic-diols underwent twofold Mitsunobu reaction (Ph3P/DEAD/HN3) followed by catalytic hydrogenation forming stereospecifically the corresponding primary vicinal ...