4.8 Article

Pyridinium 1,1′-Binaphthyl-2,2′-disulfonates as Highly Effective Chiral Bronsted Acid-Base Combined Salt Catalysts for Enantioselective Mannich-Type Reaction

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 130, Issue 50, Pages 16858-+

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ja806875c

Keywords

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Funding

  1. JSPS, KAKENHI [20245022]
  2. MEXT [19750072]
  3. G-COE Program of MEXT
  4. Toray Science Foundation
  5. Iketani Science and Technology Foundation
  6. Izumi Science and Technology Foundation
  7. JSPS
  8. Grants-in-Aid for Scientific Research [20245022, 19750072] Funding Source: KAKEN

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We have established, for the first time, a practical synthesis of chiral 1,1'-binaphthyl-2,2'-disulfonic acid (BINSA 1) from inexpensive BINOL. An efficient enantioselective catalysis in the Mannich-type reactions of diketones and ketoester equivalents with aldimines was developed using chiral 1-achiral, 2,6-diarylpyridine (2) combined salts, which acted as convenient chiral tailor-made Bronsted acid-base organocatalysts in situ.

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