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Setting all‐carbon quaternary stereocenters with stereospecific, nickel‐catalyzed cross couplings
Author(s) -
Duke Alana D.,
Pound Sarah M.,
Xu Jianyu,
Basch Corey H.,
Hoerrner Megan E.,
Bampo Earl M.,
Watson Mary P.
Publication year - 2018
Publication title -
the faseb journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.709
H-Index - 277
eISSN - 1530-6860
pISSN - 0892-6638
DOI - 10.1096/fasebj.2018.32.1_supplement.531.21
Subject(s) - stereocenter , pinacol , stereospecificity , aryl , chemistry , combinatorial chemistry , enantioselective synthesis , catalysis , yield (engineering) , nickel , stereochemistry , organic chemistry , materials science , alkyl , metallurgy
Formation of quaternary stereocenters is an essential goal for organic chemistry due to these centers' presence in numerous drugs and their importance in biological activity. Transition metal catalysis offers a unique approach to this challenge, but previous attempts have been limited in either scope or enantiomeric enrichment. We are introducing a stereospecific Suzuki cross coupling of enantioenriched benzyl alcohol derivatives via C‐O bond activation that yields quaternary stereocenters with both aryl and vinyl substituents. Using benzylic carboxylates available in high enantiopurity, an air‐stable, inexpensive nickel source, and pinacol boronates, the reaction yields products in high yield and enantioenrichment and can tolerate a wide range of functional groups, including heteroaromatics. The optimization and scope of these reactions will be presented. Support or Funding Information The National Institutes of Health (R01 GM111820) is gratefully acknowledged. This abstract is from the Experimental Biology 2018 Meeting. There is no full text article associated with this abstract published in The FASEB Journal .