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

Teruhiko Ishikawa; Toshiaki Aikawa; Shinichiro Watanabe; Seiki Saito

doi:10.1021/ol0616485

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 S_N1 and intramolecular Michael addition

Teruhiko Ishikawa, Toshiaki Aikawa, Shinichiro Watanabe, Seiki Saito

Research output: Contribution to journal › Article › peer-review

26 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	3881-3884
Number of pages	4
Journal	Organic Letters
Volume	8
Issue number	17
DOIs	https://doi.org/10.1021/ol0616485
Publication status	Published - Aug 17 2006

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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Ishikawa, T., Aikawa, T., Watanabe, S., & Saito, S. (2006). 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 S_N1 and intramolecular Michael addition. Organic Letters, 8(17), 3881-3884. https://doi.org/10.1021/ol0616485

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 S_N1 and intramolecular Michael addition. / Ishikawa, Teruhiko; Aikawa, Toshiaki; Watanabe, Shinichiro et al.
In: Organic Letters, Vol. 8, No. 17, 17.08.2006, p. 3881-3884.

Research output: Contribution to journal › Article › peer-review

Ishikawa, T, Aikawa, T, Watanabe, S & Saito, S 2006, '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 S_N1 and intramolecular Michael addition', Organic Letters, vol. 8, no. 17, pp. 3881-3884. https://doi.org/10.1021/ol0616485

Ishikawa, Teruhiko ; Aikawa, Toshiaki ; Watanabe, Shinichiro et al. / 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 S_N1 and intramolecular Michael addition. In: Organic Letters. 2006 ; Vol. 8, No. 17. pp. 3881-3884.

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