A lactam-derived vinyl boronate as a stable and crystalline reagent for the synthesis of 2--substituted piperidines by Pd-catalyzed coupling reactions
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Ferrali, A
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Univ Florence, Dipartimento Chim Organ U Schiff, I-50019 Sesto Fiorentino, ItalyUniv Florence, Dipartimento Chim Organ U Schiff, I-50019 Sesto Fiorentino, Italy
Ferrali, A
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Guarna, A
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Univ Florence, Dipartimento Chim Organ U Schiff, I-50019 Sesto Fiorentino, ItalyUniv Florence, Dipartimento Chim Organ U Schiff, I-50019 Sesto Fiorentino, Italy
Guarna, A
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Lo Galbo, F
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Univ Florence, Dipartimento Chim Organ U Schiff, I-50019 Sesto Fiorentino, ItalyUniv Florence, Dipartimento Chim Organ U Schiff, I-50019 Sesto Fiorentino, Italy
Lo Galbo, F
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Occhiato, EG
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Univ Florence, Dipartimento Chim Organ U Schiff, I-50019 Sesto Fiorentino, ItalyUniv Florence, Dipartimento Chim Organ U Schiff, I-50019 Sesto Fiorentino, Italy
Occhiato, EG
[1
]
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[1] Univ Florence, Dipartimento Chim Organ U Schiff, I-50019 Sesto Fiorentino, Italy
A delta-valerolactam-derived vinyl triflate has been converted into the corresponding vinyl boronate by Pd-catalyzed coupling with bis(pinacolato)diboron, which results in all umpolung. This boronate efficiently couples under Pd catalysis with aryl and heteroaryl bromides to give the corresponding 2-substituted piperidines ill excellent yields. (C) 2004 Elsevier Ltd. All rights reserved.