Journal
ORGANIC LETTERS
Volume 14, Issue 12, Pages 3134-3137Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol301219c
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- National Science Council of the Republic of China
- Kaohsiung Medical University Research Foundation
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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-clig 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.
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