Tetrahedron: Asymmetry

Enantiopure erythro-and threo-1-aryl-1-[2-pyrrolidyl]-methanols: synthesis from l-proline

A Solladié-Cavallo, K Azyat, M Schmitt, R Welter

Index: Solladie-Cavallo, Arlette; Azyat, Khalid; Schmitt, Michel; Welter, Richard Tetrahedron Asymmetry, 2005 ,  vol. 16,  # 5  p. 1055 - 1060

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Citation Number: 5

Abstract

Enantiopure (1R, 2S)-erythro-and (1S, 2S)-threo-isomers of four new aryl-pyrrolidyl alcohols 5aH, 5aMe, 5bH and 5bMe have been obtained in five steps from (−)-(S)-proline and fully characterized. The oxidation of alcohol 8 into aldehyde 9 was the most difficult step and racemization occurs during Swern oxidation but this difficulty can be overcome by using SO3/pyridine as oxidant. Diastereomer I of the protected amino alcohol 10a crystallized ...