Organocatalytic asymmetric synthesis of quinine and quinidine

…, A Nakano, K Takahashi, J Ishihara, S Hatakeyama

Index: Sarkar, Shaheen M.; Taira, Yuko; Nakano, Ayako; Takahashi, Keisuske; Ishihara, Jun; Hatakeyama, Susumi Tetrahedron Letters, 2011 ,  vol. 52,  # 8  p. 923 - 927

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Citation Number: 17

Abstract

Quinine and quinidine were synthesized by a highly enantio-and stereoselective approach starting from a proline-catalyzed asymmetric cycloaldolization of benzyl bis (2-formylethyl) carbamate which gave a 70: 30 mixture of (3R, 4R)-N-Cbz-3-hydroxymethyl-4- hydroxypiperidine (96% ee) and its 4S-epimer (92% ee) in 94% yield after in situ NaBH4 reduction.