Efficient synthesis of 1,3,5-trisubstituted (pyrrol-2-yl) acetic acid esters via dual nucleophilic reactions of sulfonamides or carbamate with 4-trimethyl-siloxy-(5E)-hexen-2-ynoates:: Lewis acid catalyzed SN1 and intramolecular Michael addition

被引：26

作者：

Ishikawa, Teruhiko ^{[1
]}

Aikawa, Toshiaki ^{[1
]}

Watanabe, Shinichiro ^{[1
]}

Saito, Seiki ^{[1
]}

机构：

[1] Okayama Univ, Dept Med & Bioengn Sci, Grad Sch Nat Sci & Technol, Okayama 7008530, Japan

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 17期

关键词：

D O I：

10.1021/ol0616485

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Carbamates or sulfonamides have proven to regioselectively attack 2-propynyl-allyl hybrid cations, generated by the action of TMSOTf on 4-(trimethylsioxy)hex-5-en-2-ynoates, to afford conjugated 6-aminohex-4-en-2-ynoates in which an intramolecular amino-Michael reaction took place, leading to pyrrole frameworks. In particular, the sulfonamides gave 1-sulfonylpyrroles in one pot.

引用

页码：3881 / 3884

页数：4

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