Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 55, Issue 31, Pages 8970-8974Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201603929
Keywords
asymmetric catalysis; Bronsted acids; chiral phosphoric acids; Mukaiyama-Mannich reactions; quaternary stereogenic centers
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Funding
- ACT-C, JST
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A new BINOL-derived chiral phosphoric acid bearing 2,4,6-trimethyl-3,5-dinitrophenyl substituents at the 3,3'-positions was developed. The utility of this chiral phosphoric acid is demonstrated by a highly enantioselective (ee up to >99%) and diastereoselective (syn/anti up to >99: 1) asymmetric Mukaiyama-Mannich reaction of imines with a wide range of ketene silyl acetals. Moreover, this method was successfully applied to the construction of vicinal tertiary and quaternary stereogenic centers with excellent diastereo- and enantioselectivity. Significantly, BINOL-derived N-triflyl phosphoramide constitutes a complementary catalyst system that allows the title reaction to be applied to more challenging imines without an N-(2-hydroxyphenyl) moiety.
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