Synlett 2013; 24(5): 625-629
DOI: 10.1055/s-0032-1318300
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© Georg Thieme Verlag Stuttgart · New York

Diastereoselective Synthesis of 1,3-syn-Oxazines via a Tandem Hemiaminalization and Tsuji–Trost Reaction

Bin Tang
a   Ruprecht-Karls-Universität Heidelberg, Institut für Organische Chemie, INF 270, 69120 Heidelberg, Germany
,
Liang Wang
a   Ruprecht-Karls-Universität Heidelberg, Institut für Organische Chemie, INF 270, 69120 Heidelberg, Germany
,
Dirk Menche*
b   Rheinische Friedrich-Wilhelms-Universität Bonn, Institut für Organische Chemie und Biochemie, Gerhard-Domagk-Str 1, 53121 Bonn, Germany   Fax: +49(228)735813   eMail: dirk.menche@uni-bonn.de
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Received: 03. Dezember 2012

Accept after revision: 31. Januar 2013

Publikationsdatum:
18. Februar 2013 (online)


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Abstract

A novel domino sequence for the rapid assembly of 1,3-syn-substituted oxazines is reported. Mechanistically, the one-pot procedure is based on a three-step sequential process involving a hemiaminalization and Tsuji–Trost reaction. The process generates up to two new stereogenic centers in a concise and convergent fashion from simple and readily available starting materials.

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