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Configurational Control of Benzyl Carbanion–Copper Complexes by Sulfinyl Groups: Synthesis of Optically Pure Allenes with Central and Axial Chirality
Author(s) -
García Ruano José Luis,
Marcos Vanesa,
Alemán José
Publication year - 2008
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.200802158
Subject(s) - allene , propargyl , carbanion , chemistry , reagent , chirality (physics) , regioselectivity , enantiomer , stereoselectivity , stereochemistry , kinetic resolution , enantioselective synthesis , combinatorial chemistry , organic chemistry , catalysis , physics , particle physics , chiral symmetry breaking , quantum chromodynamics , nambu–jona lasinio model
Lean, mean, chiral allene : Optically pure complexes 2 react with propargyl bromides and mesylates 1 to afford the title products (see scheme; LG=leaving group). The regioselectivity and the configuration of the chiral axis are completely controlled, and the stereoselectivity at the benzylic position is high. Kinetic resolution of racemic propargyl mesylates can also be achieved with these reagents.