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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.