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The Prins Reaction Using Ketones: Rationalization and Application toward the Synthesis of the Portentol Skeleton
- Source :
- Organic Letters, Organic Letters, 2012, 14 (1), pp.58-61. ⟨10.1021/ol202829u⟩, Organic Letters, American Chemical Society, 2012, 14 (1), pp.58-61. ⟨10.1021/ol202829u⟩
- Publication Year :
- 2011
- Publisher :
- American Chemical Society (ACS), 2011.
-
Abstract
- International audience; We report a TMSI-promoted Prins cyclization reaction with ketones as carbonyl partners to prepare polysubstituted chiral spirotetrahydropyrans. In the presence of racemic 2-methylcyclohexanone a dynamic kinetic resolution occurred affording one stereoisomer. The observed enantiospecificity has been rationalized by DFT calculation.
- Subjects :
- MESH: Molecular Structure
MESH: Ketones
010402 general chemistry
01 natural sciences
Biochemistry
Kinetic resolution
Computational chemistry
Spiro Compounds
MESH: Cyclization
MESH: Pyrans
[SDV.BBM.BC]Life Sciences [q-bio]/Biochemistry, Molecular Biology/Biochemistry [q-bio.BM]
Physical and Theoretical Chemistry
Pyrans
Molecular Structure
MESH: Kinetics
010405 organic chemistry
Chemistry
Organic Chemistry
Rationalization (psychology)
Stereoisomerism
Ketones
Prins reaction
MESH: Stereoisomerism
0104 chemical sciences
Kinetics
MESH: Spiro Compounds
Cyclization
Subjects
Details
- ISSN :
- 15237052 and 15237060
- Volume :
- 14
- Database :
- OpenAIRE
- Journal :
- Organic Letters
- Accession number :
- edsair.doi.dedup.....5fd4689a2d542bbf7652661764550e13
- Full Text :
- https://doi.org/10.1021/ol202829u