Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 58, Issue 40, Pages 14104-14109Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201906681
Keywords
asymmetric catalysis; C-H allylation; aza-Wittig rearrangement; rearomatization; TADDOL phosphites
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Funding
- SERB [EMR/2015/000711]
- UGC
- CSIR-NCL [MLP030926]
- central NMR facility, NCL
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A phosphite-mediated [2,3]-aza-Wittig rearrangement has been developed for the regio- and enantioselective allylic alkylation of six-membered heteroaromatic compounds (azaarenes). The nucleophilic phosphite adducts of N-allyl salts undergo a stereoselective base-mediated aza-Wittig rearrangement and dissociation of the chiral phosphite for overall C-H functionalization of azaarenes. This method provides efficient access to tertiary and quaternary chiral centers in isoquinoline, quinoline, and pyridine systems, tolerating a broad variety of substituents on both the allyl part and azaarenes. Catalysis with chiral phosphites is also demonstrated with synthetically useful yields and enantioselectivities.
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