Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 56, Issue 48, Pages 15358-15362Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201709224
Keywords
asymmetric catalysis; aza-Friedel-Crafts reactions; ketimines; organocatalysis; pyrazolone
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Funding
- European Research Council (ERC) [320493]
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N-Boc ketimines derived from pyrazolin-5-ones were explored to develop an unprecedented domino aza-Friedel-Crafts/N,O-acetalization reaction with 2-naphthols. The novel method requires a catalyst loading of only 0.5mol% of a bifunctional squaramide catalyst, is scalable to gram amounts, and provides a new series of furanonaphthopyrazolidinone derivatives bearing two vicinal tetra-substituted stereogenic centers in excellent yields (95-98%) and stereoselectivity (>99:1 d.r. and 97-98% ee). A different reactivity was observed in the case of 1-naphthols and other electron-rich phenols, which led to the aza-Friedel-Crafts adducts in 70-98% yield and 47-98% ee.
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