Highly Enantioselective Control of Dynamic Cascade Transformations by Dual Catalysis : Asymmetric Synthesis of Polysubstituted Spirocyclic Oxindoles

• The highly enantioselective (up to >99.5:0.5 er) synthesis of polysubstituted spirocyclic oxindoles with four new contiguous stereocenters, including the spiro all-carbon quaternary center, is disclosed. It is accomplished by the highly stereoselective control of a dynamic conjugate/intramolecular allylic alkylation relay sequence based on the synergistic cooperation of metal and chiral amine catalysts in which the careful selection of organic Nand, metal complex, and chiral amine is essential. The intermolecular C-C bond-forming step occurred only when both the metal and chiral amine catalysts were present.

Ämnesord

NATURVETENSKAP  -- Kemi (hsv//swe)

NATURAL SCIENCES  -- Chemical Sciences (hsv//eng)

Nyckelord

asymmetric cocatalysis

alpha

beta-unsaturated aldehydes

dynamic transformations

polysubstituted

spirocyclic oxindoles

all-carbon quaternary stereocenter

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