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Versatile C(sp 2 )−C(sp 3 ) Ligand Couplings of Sulfoxides for the Enantioselective Synthesis of Diarylalkanes
Author(s) -
Dean William M.,
Šiaučiulis Mindaugas,
Storr Thomas E.,
Lewis William,
Stockman Robert A.
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201602264
Subject(s) - reagent , enantioselective synthesis , chemistry , aryl , ligand (biochemistry) , yield (engineering) , combinatorial chemistry , enantiomer , hydride , coupling reaction , stereoisomerism , enantiomeric excess , metal , medicinal chemistry , stereochemistry , catalysis , organic chemistry , materials science , biochemistry , alkyl , receptor , metallurgy
The reaction of chiral (hetero)aryl benzyl sulfoxides with Grignard reagents affords enantiomerically pure diarylalkanes in up to 98 % yield and greater than 99.5 % enantiomeric excess. This ligand coupling reaction is tolerant to multiple substitution patterns and provides access to diverse areas of chemical space in three operationally simple steps from commercially available reagents. This strategy provides orthogonal access to electron‐deficient heteroaromatic compounds, which are traditionally synthesized by transition metal catalyzed cross‐couplings, and circumvents common issues associated with proto‐demetalation and β‐hydride elimination.