Journal
TETRAHEDRON LETTERS
Volume 54, Issue 21, Pages 2699-2702Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2013.03.076
Keywords
4-Aryl-1,2,3,4-tetrahydroisoquinolines; 5-Aryloxazolidines; Non-stabilized azomethine ylide; [3+2] Cycloaddition; Cyclization reaction
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Funding
- RFBR [12-03-31036]
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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-beta-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. (c) 2013 Elsevier Ltd. All rights reserved.
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