Synthetic and computational evaluation of regiodivergent epoxide opening for diol and polyol synthesis.
In a combined synthetic and computational study, the factors governing the selectivity of the titanocene(III)-catalyzed regiodivergent epoxide opening (REO) with Kagan's complex via electron transfer leading to derivatives of 1,2-, 1,3-, and 1,4-diols were investigated. In this manner, valuable building blocks for the synthesis of 1,3- and 1,4-diols were identified. The computational study provides crucial structural features and energies of the transition states of ring opening that are important for the design of more selective catalysts.
Kekulé-Institut für Organische Chemie und Biochemie, Universität Bonn, Gerhard Domagk Str. 1, 53121 Bonn (Germany), Fax: (+49) 0228-73-5683. andreas.gansaeuer@uni-bonn.de.
Andreas
A
Gansäuer
Peter
P
Karbaum
David
D
Schmauch
Martin
M
Einig
Lili
L
Shi
Anakuthil
A
Anoop
Frank
F
Neese
catalysis; density functional calculations; enantioselectivity; epoxides; radicals