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Catalytic Asymmetric Allylboration of Indoles and Dihydroisoquinolines with Allylboronic Acids: Stereodivergent Synthesis of up to Three Contiguous Stereocenters
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AbstractThe catalytic asymmetric allylboration of cyclic imines with γ,γ‐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.
Title: Catalytic Asymmetric Allylboration of Indoles and Dihydroisoquinolines with Allylboronic Acids: Stereodivergent Synthesis of up to Three Contiguous Stereocenters
Description:
AbstractThe catalytic asymmetric allylboration of cyclic imines with γ,γ‐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.
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