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Catalytic Asymmetric Allylboration of Indoles and Dihydroisoquinolines with Allylboronic Acids: Stereodivergent Synthesis of up to Three Contiguous Stereocenters
Author(s) -
Alam Rauful,
Diner Colin,
Jonker Sybrand,
Eriksson Lars,
Szabó Kálmán J.
Publication year - 2016
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201608605
Subject(s) - stereocenter , stereoselectivity , electrophile , enantiomer , catalysis , enantioselective synthesis , yield (engineering) , stereochemistry , chemistry , combinatorial chemistry , organic chemistry , materials science , metallurgy
The 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.