TY - JOUR
T1 - A Chiral Thiourea as a Template for Enantioselective Intramolecular [2 + 2] Photocycloaddition Reactions
AU - Mayr, Florian
AU - Brimioulle, Richard
AU - Bach, Thorsten
N1 - Publisher Copyright:
© 2016 American Chemical Society.
PY - 2016/8/19
Y1 - 2016/8/19
N2 - A chiral (1R,2R)-diaminocyclohexane-derived bisthiourea was found to exhibit a significant asymmetric induction in the intramolecular [2 + 2] photocycloaddition of 2,3-dihydropyridone-5-carboxylates. Under optimized conditions, the reaction was performed with visible light employing 10 mol % of thioxanthone as triplet sensitizer. Due to the different electronic properties of its carbonyl oxygen atoms, a directed binding of the substrate to the template is possible, which in turn enables an efficient enantioface differentiation.
AB - A chiral (1R,2R)-diaminocyclohexane-derived bisthiourea was found to exhibit a significant asymmetric induction in the intramolecular [2 + 2] photocycloaddition of 2,3-dihydropyridone-5-carboxylates. Under optimized conditions, the reaction was performed with visible light employing 10 mol % of thioxanthone as triplet sensitizer. Due to the different electronic properties of its carbonyl oxygen atoms, a directed binding of the substrate to the template is possible, which in turn enables an efficient enantioface differentiation.
UR - http://www.scopus.com/inward/record.url?scp=84983320513&partnerID=8YFLogxK
U2 - 10.1021/acs.joc.6b01039
DO - 10.1021/acs.joc.6b01039
M3 - Article
AN - SCOPUS:84983320513
SN - 0022-3263
VL - 81
SP - 6965
EP - 6971
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 16
ER -