Tetrahedron Letters p. 9121 - 9124 (1998)
Update date:2022-08-03
Topics:
Lacoste, Jean-Eric
Soucy, Chantal
Rochon, Fernande D.
Breau, Livain
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 of this auxiliary was demonstrated by highly diastereoselective (i.e. 90% de) 1,3-dipolar cycloadditions with nitrile oxides.
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