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A study of the stereochemistry of the acid-catalyzed cyclization between (-)-8-tosylaminomenthol (derived from (+)-pulegone) and acrolein diethyl acetal afforded two novel chiral perhydro-1,3-benzoxazine isomers 4a and 4b. Catalyst type as well as the reaction conditions dramatically affected the isomeric ratio. An X-ray crystal structure of 4a established a chair-boat conformation. The usefulness...
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