A diastereoselective construction of pyrazinoisoquinoline skeletons via tandem cyclization of phenylalanine derivatives: a facile synthesis of optically active pyrazinoisoquinolines

A facile and stereocontrolled construction of optically active pyrazinoisoquinoline skeletons based on tandem cyclization of enantiopure phenylalanine derivatives was examined. The reaction provided optically active 6,11b-trans pyrazinoisoquinoline ring systems in excellent diastereoselectivity, and...

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Veröffentlicht in:	Tetrahedron 2014-06, Vol.70 (25), p.3864-3870
Hauptverfasser:	Seki, Maki, Ogiku, Tsuyoshi
Format:	Artikel
Sprache:	eng
Schlagworte:	1,3-Chirality transfer Construction Derivatives N-Acyliminium ion Optical activity Phenylalanine Pictet–Spengler cyclization Pyrazinoisoquinolines Synthesis (chemistry) Tetrahedrons
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Zusammenfassung:	A facile and stereocontrolled construction of optically active pyrazinoisoquinoline skeletons based on tandem cyclization of enantiopure phenylalanine derivatives was examined. The reaction provided optically active 6,11b-trans pyrazinoisoquinoline ring systems in excellent diastereoselectivity, and this method was applicable to the cyclization of phenylalanine derivatives with diverse substituents. [Display omitted]
ISSN:	0040-4020 1464-5416
DOI:	10.1016/j.tet.2014.04.045