Title of article
Facile one-pot synthesis of tetrahydroisoquinolines from amino acids via hypochlorite-mediated decarboxylation and Pictet–Spengler condensation
Author/Authors
Maresh، نويسنده , , Justin J. and Crowe، نويسنده , , Sean O. and Ralko، نويسنده , , Arthur A. and Aparece، نويسنده , , Mark D. and Murphy، نويسنده , , Casey M. and Krzeszowiec، نويسنده , , Mark and Mullowney، نويسنده , , Michael W.، نويسنده ,
Issue Information
هفته نامه با شماره پیاپی سال 2014
Pages
5
From page
5047
To page
5051
Abstract
A convenient method for oxidative decarboxylation of α-amino acids is presented. The aldehyde products may be isolated or converted to tetrahydroisoquinolines by addition of dopamine via Pictet–Spengler reaction. Racemic products are generated by phosphate buffer >300 mM to maximize regioselectivity. (S)-Enantiomer products are generated by norcoclaurine synthase reaction in maleic acid buffer to minimize chemical background reaction.
Keywords
Pictet–Spengler reaction , Norcoclaurine synthase , Tetrahydroisoquinoline alkaloids , Sodium hypochlorite
Journal title
Tetrahedron Letters
Serial Year
2014
Journal title
Tetrahedron Letters
Record number
1890571
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