CHIRAL TOLUENE-2,ALPHA-SULTAM AUXILIARIES - ASYMMETRIC ALKYLATIONS, ACYLATIONS AND ALDOLIZATIONS OF N-ACYL DERIVATIVES

被引：86

作者：

OPPOLZER, W

RODRIGUEZ, I

STARKEMANN, C

WALTHER, E

机构：

[1] Département de Chimie Organique, Université de Genève

来源：

TETRAHEDRON LETTERS | 1990年 / 31卷 / 35期

关键词：

D O I：

10.1016/S0040-4039(00)97794-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Successive treatment of (R)-N-acylsultams 4 with NHDMS/alkyl halides or NHDMS/acyl chlorides provides alkylated or acylated products 6 or 7. Diastereoselective reductions of 7 with Zn(BH4)2 or NaHB(sBu)3 gives "syn"- or "anti"-aldols 8 or 9. Reaction of 4 with BEt3/TfOH/EtN(iPr)2 followed by addition of aromatic or aliphatic aldehydes affords diastereomerically pure "synrd-aldols 10. Non-destructive removal of auxiliary 3 from 6, 8, 9 and 10 yields enantiomerically pure products 12 to 16. © 1990.

引用

页码：5019 / 5022

页数：4

共 8 条

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