textjournal article
A New Approach to 1,4-Oxazines and 1,4-Oxazepines via Base-Promoted Exo Mode Cyclization of Alkynyl Alcohols: Mechanism and DFT Studies
Abstract
A new approach was developed to synthesize 1,4-oxazine and 1,4-oxazepine derivatives without solvent and metal. Regioselective cyclization occurred to afford exclusively the exo-dig product, and stereochemistry was studied by circular dichroism and specific optical rotation techniques. The Grignard reaction is a key synthetic step to produce high diastereomeric compounds via Cram’s rule and was well supported by DFT calculations. A hydroalkoxylation mechanism was proposed and supported by DFT calculations- Text
- Journal contribution
- Biophysics
- Biochemistry
- Molecular Biology
- Physiology
- Biotechnology
- Developmental Biology
- Infectious Diseases
- Biological Sciences not elsewhere classified
- Chemical Sciences not elsewhere classified
- Cyclization
- Mechanism
- Cram
- diastereomeric compounds
- oxazine
- Regioselective cyclization
- hydroalkoxylation mechanism
- rotation techniques
- dichroism
- DFT StudiesA
- derivative
- Grignard reaction
- approach
- DFT calculations
- Exo
- New Approach
- Mode
- stereochemistry
- Oxazepine
- oxazepine
- Alkynyl Alcohols
- Oxazine
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Last time updated on 16/03/2018
This paper was published in The Francis Crick Institute.
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