Tetrahedron Letters

Reaction of 5-aryloxazolidines with arylmagnesium bromides as a new route to N-benzyl-β-hydroxyphenethylamines as starting materials for the preparation of 4-aryl- …

VS Moshkin, VY Sosnovskikh

Index: Moshkin, Vladimir S.; Sosnovskikh, Vyacheslav Ya. Tetrahedron Letters, 2013 , vol. 54, # 21 p. 2699 - 2702

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Citation Number: 12

Abstract

Benzaldehydes react smoothly with the non-stabilized azomethine ylide derived from sarcosine and formaldehyde to form 5-aryloxazolidines as intermediates, which undergo ring-opening to give N-benzyl-β-hydroxyphenethylamines in good yields by the action of arylmagnesium bromides. Their subsequent acid-catalyzed cyclization into 4-aryl-1, 2, 3, 4- tetrahydroisoquinolines was performed in moderate to good yields.