Synlett 2016; 27(06): 941-945
DOI: 10.1055/s-0035-1560548
letter
© Georg Thieme Verlag Stuttgart · New York

C 2-Symmetric Chiral Sulfoxide-Mediated Intermolecular Interrupted Pummerer Reaction for Enantioselective Construction of C3a-Substituted Pyrroloindolines

Masanori Tayu
Meiji Pharmaceutical University, 2-522-1, Noshio, Kiyose, Tokyo, 204-8588, Japan   eMail: kawasaki@my-pharm.ac.jp
,
Yui Suzuki
Meiji Pharmaceutical University, 2-522-1, Noshio, Kiyose, Tokyo, 204-8588, Japan   eMail: kawasaki@my-pharm.ac.jp
,
Kazuhiro Higuchi*
Meiji Pharmaceutical University, 2-522-1, Noshio, Kiyose, Tokyo, 204-8588, Japan   eMail: kawasaki@my-pharm.ac.jp
,
Tomomi Kawasaki*
Meiji Pharmaceutical University, 2-522-1, Noshio, Kiyose, Tokyo, 204-8588, Japan   eMail: kawasaki@my-pharm.ac.jp
› Institutsangaben
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Publikationsverlauf

Received: 04. Oktober 2015

Accepted after revision: 22. Oktober 2015

Publikationsdatum:
07. Januar 2016 (online)


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Abstract

The first example of an enantioselective intermolecular interrupted Pummerer reaction has been developed by the utilization of a C 2-symmetric chiral sulfoxide. The reaction was used for the enantioselective synthesis of C3a-substituted pyrroloindolines in a one-pot procedure starting from tryptamine. The synthetic utility of the reaction was further demonstrated by its application to the highly concise total synthesis of (+)-psychotriasine.

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