Inversion of diastereoselectivity under high pressure conditions: Diels–Alder reactions of 12-N-substituted derivatives of (−)-cytisine with N-phenylmaleimide

[Display omitted] Diels–Alder adducts of 12-N-substituted derivatives of (−)-cytisine with N-phenylmaleimide were synthesized. The conditions of effective diastereodifferentiation were found: the thermal Diels–Alder reaction of 12-N-substituted derivatives of (−)-cytisine with N-phenylmaleimide lead...

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Published inTetrahedron: asymmetry Vol. 26; no. 14; pp. 732 - 737
Main Authors Tsypysheva, Inna P., Borisevich, Sophia S., Lobov, Alexander N., Kovalskaya, Alena V., Shamukaev, Vadim V., Safiullin, Rustam L., Khursan, Sergey L.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 31.07.2015
Elsevier
Subjects
Chemistry
Chemistry, Inorganic & Nuclear
Chemistry, Organic
Chemistry, Physical
Physical Sciences
Science & Technology
ORGANIC-SYNTHESIS
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Summary:[Display omitted] Diels–Alder adducts of 12-N-substituted derivatives of (−)-cytisine with N-phenylmaleimide were synthesized. The conditions of effective diastereodifferentiation were found: the thermal Diels–Alder reaction of 12-N-substituted derivatives of (−)-cytisine with N-phenylmaleimide leads to 3aS, 4R, 12aR, 12bS adducts, while under high pressure, adducts with 3aR, 4S, 12aS, 12bR configurations of new asymmetric centers are formed. The effect of high pressure on the diastereoselectivity of Diels–Alder reaction was rationalized by theoretical DFT calculations.
ISSN:0957-4166
1362-511X
DOI:10.1016/j.tetasy.2015.06.005