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Enantioselective synthesis of chiral carbocyclic pyrimidine nucleosides via asymmetric cyclopropanation
- Source :
- Tetrahedron Letters. 60:151183
- Publication Year :
- 2019
- Publisher :
- Elsevier BV, 2019.
-
Abstract
- An efficient method to construct chiral cyclopropyl pyrimidine carbocyclic nucleoside analogues bearing a quaternary center was developed via asymmetric Michael-initiated cyclopropanation. The axis chirality was observed in cyclopropyl pyrimidine carbocyclic nucleoside analogues for the first time, which was caused by the rotationally restricted N C bond in N-COPh moiety. Using (DHQD)2AQN as the organocatalyst, diverse cyclopropyl pyrimidine carbocyclic nucleoside analogues were generated in 76–93% yields and 73–96% ee.
- Subjects :
- Pyrimidine
010405 organic chemistry
Cyclopropanation
Stereochemistry
Organic Chemistry
Enantioselective synthesis
010402 general chemistry
01 natural sciences
Biochemistry
0104 chemical sciences
chemistry.chemical_compound
chemistry
Carbocyclic nucleoside
Drug Discovery
Moiety
Chirality (chemistry)
Subjects
Details
- ISSN :
- 00404039
- Volume :
- 60
- Database :
- OpenAIRE
- Journal :
- Tetrahedron Letters
- Accession number :
- edsair.doi...........aa91e0eed96dc55ea9f6bc251eabe215