A Novel Three‐Component [3+2] Cycloannulation Process for the Rapid and Highly Stereoselective Synthesis of Pyrrolobenzoxazoles | Zendy

Boomhoff Michael | Zendy; Schneider Christoph | Zendy

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A Novel Three‐Component [3+2] Cycloannulation Process for the Rapid and Highly Stereoselective Synthesis of Pyrrolobenzoxazoles

Author(s) -

Boomhoff Michael,

Schneider Christoph

Publication year - 2012

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.201200405

Subject(s) - stereoselectivity , component (thermodynamics) , scandium , trimethylsilyl , proline , chemistry , combinatorial chemistry , catalysis , process (computing) , stereochemistry , organic chemistry , computer science , amino acid , physics , programming language , thermodynamics , biochemistry

Four new σ bonds and two chiral centers are formed in a novel three‐component, one‐pot [3+2] cycloannulation process, which gives pyrrolobenzoxazoles directly in good yields and with excellent diastereoselectivity (see scheme, TMS=trimethylsilyl). The products could be converted into proline derivatives with full stereochemical control. A chiral scandium complex catalyzed the formation of the products with up to 83 % ee.

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