The synthesis of optically pure cross-conjugated cyclopentadienones is readily achieved in two steps via a one-pot alkylcuprate addition/aldol condensation/dehydration sequence using racemic or enantioenriched endo-3a,4,7,7a-tetrahydro-1H-4,7-methano-inden-1-ones followed by microwave-mediated Lewis acid-catalysed retro Diels-Alder reaction. An alternative route involving a modified Baylis-Hillman protocol followed by conjugate addition with alkylcuprates and a retro Diels-Alder reaction was also investigated. © 2004 Elsevier Ltd. All rights reserved.

Eddolls, J., Iqbal, M., Roberts, S., Santoro, M.g. (2004). Preparation of optically pure cross-conjugated cyclopentadienones. TETRAHEDRON, 60(11), 2539-2550 [10.1016/j.tet.2004.01.047].

Preparation of optically pure cross-conjugated cyclopentadienones

SANTORO, MARIA GABRIELLA
2004-01-01

Abstract

The synthesis of optically pure cross-conjugated cyclopentadienones is readily achieved in two steps via a one-pot alkylcuprate addition/aldol condensation/dehydration sequence using racemic or enantioenriched endo-3a,4,7,7a-tetrahydro-1H-4,7-methano-inden-1-ones followed by microwave-mediated Lewis acid-catalysed retro Diels-Alder reaction. An alternative route involving a modified Baylis-Hillman protocol followed by conjugate addition with alkylcuprates and a retro Diels-Alder reaction was also investigated. © 2004 Elsevier Ltd. All rights reserved.
2004
Pubblicato
Rilevanza internazionale
Articolo
Sì, ma tipo non specificato
Settore MAT/05 - ANALISI MATEMATICA
English
4-Alkyl 5-alkyli-denecyclopent-2-enones; Baylis-Hillman reaction; Microwave-promoted reactions; retro-Diels-Alder reaction
Eddolls, J., Iqbal, M., Roberts, S., Santoro, M.g. (2004). Preparation of optically pure cross-conjugated cyclopentadienones. TETRAHEDRON, 60(11), 2539-2550 [10.1016/j.tet.2004.01.047].
Eddolls, J; Iqbal, M; Roberts, S; Santoro, Mg
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2108/32794
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