Brønsted Acid Catalyzed [3+2]‐Cycloaddition of 2‐Vinylindoles with In Situ Generated 2‐Methide‐2 H ‐indoles: Highly Enantioselective Synthesis of Pyrrolo[1,2‐ a ]indoles | Zendy

Bera Kalisankar | Zendy; Schneider Christoph | Zendy

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Brønsted Acid Catalyzed [3+2]‐Cycloaddition of 2‐Vinylindoles with In Situ Generated 2‐Methide‐2 H ‐indoles: Highly Enantioselective Synthesis of Pyrrolo[1,2‐ a ]indoles

Author(s) -

Bera Kalisankar,

Schneider Christoph

Publication year - 2016

Publication title -

chemistry – a european journal

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.687

H-Index - 242

eISSN - 1521-3765

pISSN - 0947-6539

DOI - 10.1002/chem.201601020

Subject(s) - enantioselective synthesis , stereocenter , diastereomer , chemistry , cycloaddition , catalysis , phosphoric acid , brønsted–lowry acid–base theory , in situ , organocatalysis , stereochemistry , combinatorial chemistry , organic chemistry

Pyrrolo[1,2‐ a ]indoles are privileged structural elements of many natural products and pharmaceuticals. An efficient one‐step process for their highly diastereo‐ and enantioselective synthesis, comprising a direct [3+2]‐cycloaddition, has been developed. A chiral BINOL‐derived phosphoric acid catalyzes the reaction of in situ‐generated 2‐methide‐2 H ‐indoles with 2‐vinylindoles, furnishing the target products incorporating three contiguous stereogenic centers as single diastereoisomers and with excellent yields and enantioselectivities.

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