Catalytic Asymmetric Allylboration of Indoles and Dihydroisoquinolines with Allylboronic Acids : Stereodivergent Synthesis of up to Three Contiguous Stereocenters

• The catalytic asymmetric allylboration of cyclic imines with gamma,gamma-disubstituted allylboronic acids provides products with adjacent stereocenters in high yield and stereoselectivity. Various electrophiles, including 3,4-dihydroisoquinolines and indoles, were prenylated in a fully stereodivergent fashion by switching the E/Z geometry of the allylboronate and/or the enantiomer of the BINOL catalyst. 3-Methylindole provided products with three adjacent stereocenters with high stereoselectivity in one synthetic operation.

Ämnesord

NATURVETENSKAP  -- Kemi (hsv//swe)

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

Nyckelord

allylboration

asymmetric catalysis

indoles

organocatalysis

stereoselectivity

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