Sequential Olefinations on 2-Arylmethylidene-2-phosphonoacetates: A One-Pot Highly Stereoselective Synthesis of 1,2,3-Trisubstituted 1,3-Butadienes

Sequential Olefinations on 2-Arylmethylidene-2-phosphonoacetates: A One-Pot Highly Stereoselective Synthesis of 1,2,3-Trisubstituted 1,3-Butadienes

An efficient one-pot synthetic protocol for the preparation of 1,2,3-trisubstituted dienes by a sequential addition of 2-arylmethylidene-2-phosphonoacetates and various aldehydes to trimethylsulfonium iodide/sodium dimsylate in DMSO–THF has been developed. The dienes were produced with very high ste...

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Veröffentlicht in:Bulletin of the Chemical Society of Japan 2004-11, Vol.77 (11), p.2099-2100
Hauptverfasser: Date, Sonali M, Ghosh, Sunil K
Format: Artikel
Sprache:eng
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Zusammenfassung:An efficient one-pot synthetic protocol for the preparation of 1,2,3-trisubstituted dienes by a sequential addition of 2-arylmethylidene-2-phosphonoacetates and various aldehydes to trimethylsulfonium iodide/sodium dimsylate in DMSO–THF has been developed. The dienes were produced with very high stereoselectivity preferring for the (Z)-isomer.
ISSN:0009-2673
1348-0634
DOI:10.1246/bcsj.77.2099