2001-49-2Relevant articles and documents
Why a proximity-induced Diels-Alder reaction is so fast
Krenske, Elizabeth H.,Perry, Emma W.,Jerome, Steven V.,Maimone, Thomas J.,Baran, Phil S.,Houk
scheme or table, p. 3016 - 3019 (2012/10/07)
Unlike normal Diels-Alder reactions of acyclic alkadienes with alkenes, the vinylbicyclo[2.2.2]octene employed in the Baran total synthesis of vinigrol undergoes a quantitative Diels-Alder reaction with a tethered alkene at room temperature. Density functional theory calculations reveal that this unprecedented reactivity originates from a combination of preorganization, diene strain, and tether stabilization.
Experimental determination of the activation parameters and stereoselectivities of the intramolecular Diels-Alder reactions of 1,3,8-nonatriene, 1,3,9-decatriene, and 1,3,10-undecatriene and transition state modeling with the Monte Carlo-Jumping between Wells/molecular dynamics method
Diedrich, Matthias K.,Kl?rner, Frank-Gerrit,Beno, Brett R.,Houk,Senderowitz, Hanoch,Still, W. Clark
, p. 10255 - 10259 (2007/10/03)
Experimental activation parameters for the intramolecular Diels-Alder reactions of 1,3,8-nonatriene, 1,3,9-decatriene, and 1,3,10-undecatriene have been measured, and the Monte Carlo-Jumping between Wells/Stochastic Dynamics [MC(JBW)/SD] method, which gives relative free energies of activation, was tested as a means to predict stereoselectivities. The predictions are compared to experimental results, and to predictions from quantum and molecular mechanics methods.
Synthesis of the Pyrroloisoquinoline Substructure of the Manzamine Family of Alkaloids
Hart, David J.,McKinney, Jeffrey A.
, p. 2611 - 2614 (2007/10/02)
The first synthesis of the tricyclic pyrroloisoquinoline substructure of manzamines A, B, E and F is described.Reductive alkylation of benzoic acid followed by a 3-aza-6-heptenyl radical cyclization gave octahydroisoquinoline 9.An electrophile init