Tetramethylnorbornadiene, a versatile alkene for cyclopentenone synthesis through intermolecular Pauson-Khand reactions.
1,2,3,4-Tetramethyl-bicyclo[2.2.1]hepta-2,5-diene (TMNBD, for tetramethylnorbornadiene) has been prepared and used successfully as an acetylene equivalent in the synthesis of substituted cyclopentenones. TMNBD is easily accessible on a multigram scale and displays excellent reactivity toward the intermolecular Pauson-Khand reaction. Conjugate additions on the resulting tricyclic compounds proceed with exquisite diastereoselectivity. The retro-Diels-Alder reaction of these TMNBD derivatives occurs under much smoother conditions than those required for its norbornadiene homologues.
Unitat de Recerca en Síntesi Asimètrica (URSA-PCB), Institute for Research in Biomedicine and Departament de Química Orgànica, Universitat de Barcelona, c/Baldiri Reixac, 10, E-08028 Barcelona, Spain.
Marc
M
Revés
Agustí
A
Lledó
Yining
Y
Ji
Emma
E
Blasi
Antoni
A
Riera
Xavier
X
Verdaguer
D003517:Cyclopentanes / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009636:Norbornanes / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism
D003517:Cyclopentanes; D009636:Norbornanes; C576101:tetramethylnorbornadiene; C013905:cyclopentenone