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Synthetic and Computational Evaluation of Regiodivergent Epoxide Opening for Diol and Polyol Synthesis
Author(s) -
Gansäuer Andreas,
Karbaum Peter,
Schmauch David,
Einig Martin,
Shi Lili,
Anoop Anakuthil,
Neese Frank
Publication year - 2014
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201402159
Subject(s) - epoxide , diol , polyol , selectivity , chemistry , catalysis , ring (chemistry) , combinatorial chemistry , transition state , stereochemistry , computational chemistry , organic chemistry , polyurethane
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.