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.
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页码：5019 / 5022
页数：4
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