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Synthetic Access to All Four Stereoisomers of Oxetin
- Source :
- Journal of Organic Chemistry, Journal of Organic Chemistry, 2016, 81 (20), pp.9983-9991. ⟨10.1021/acs.joc.6b01795⟩
- Publication Year :
- 2016
- Publisher :
- American Chemical Society (ACS), 2016.
-
Abstract
- A short synthesis of all four stereoisomers of 3-amino-2-oxetanecarboxylic acid (oxetin) is described. The oxetane core is built using a Paternò-Büchi photochemical [2 + 2] cycloaddition; from the key intermediates, complementary resolution protocols provide access to enantiomerically pure oxetin and epi-oxetin on gram-scale.
- Subjects :
- [PHYS]Physics [physics]
Cycloaddition Reaction
010405 organic chemistry
Stereochemistry
Spectrum Analysis
[SDV]Life Sciences [q-bio]
Organic Chemistry
Stereoisomerism
Crystallography, X-Ray
010402 general chemistry
Oxetane
01 natural sciences
Cycloaddition
0104 chemical sciences
chemistry.chemical_compound
chemistry
Ethers, Cyclic
[CHIM]Chemical Sciences
Subjects
Details
- ISSN :
- 15206904 and 00223263
- Volume :
- 81
- Database :
- OpenAIRE
- Journal :
- The Journal of Organic Chemistry
- Accession number :
- edsair.doi.dedup.....ed2e502bd8b621b6e4f787e503ac30f4
- Full Text :
- https://doi.org/10.1021/acs.joc.6b01795