A novel reductive aminocyclization for the syntheses of chiral pyrrolidines:: stereoselective syntheses of (S)-nornicotine and 2-(2′-pyrrolidyl)-pyridines

被引：17

作者：

Loh, TP ^{[1
]}

Zhou, JR ^{[1
]}

Li, XR ^{[1
]}

Sim, KY ^{[1
]}

机构：

[1] Natl Univ Singapore, Dept Chem, Singapore 119260, Singapore

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 44期

关键词：

chiral template; aminocyclization; diastereoselectivity; reduction; synthesis;

D O I：

10.1016/S0040-4039(99)01606-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(S)-Nornicotine 2 was synthesized in four steps. A key step in the synthesis involved reductive aminocyclization of a 1,4-keloaldehyde with 2,3,4,6-tetra-O-pivaloyl-beta-D-galactosylamine 1 in the presence of sodium cyanoborohydride, diastereoselectively affording the corresponding stereoisomer 6 in 45% yield. The aminosugar moiety could be easily removed by acidic hydrolysis to furnish 2. The aminocyclization was further extended to asymmetric syntheses of novel chiral 2-(2'-pyrrolidyl)-pyridine ligands 12 and 13. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：7847 / 7850

页数：4

共 17 条

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