CHIRAL TOLUENE-2, ALPHA-SULTAM AUXILIARIES - PREPARATION AND STRUCTURE OF ENANTIOMERICALLY PURE (R)-ETHYL-2 AND (S)-ETHYL-2,1'-SULTAM

被引：155

作者：

OPPOLZER, W

WILLS, M

STARKEMANN, C

BERNARDINELLI, G

机构：

[1] Département de Chimie Organique, Université de Genève

来源：

TETRAHEDRON LETTERS | 1990年 / 31卷 / 29期

关键词：

D O I：

10.1016/S0040-4039(00)97557-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Crystalline sultams (R)-2 or (S)-2 were selectively prepared from prochiral saccharine (3) in two steps (53% overall yield) via Ru-(R)-BINAP- or Ru-(S)-BINAP catalyzed asymmetric hydrogenation of imine 4. Alternatively, pure (R)-2 was synthesized (37% overall yield) from (R)-α-phenethylamine in 4-5 steps involving the ortho-sulfination 6 → 7 and the highly diastereoselective cyclization of sulfinic acid 7 to the sulfinamide 8. X-ray diffraction analyses of sulfinamide 8 and sultam (R)-2 are presented. © 1990.

引用

页码：4117 / 4120

页数：4

共 33 条

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