TY - JOUR
T1 - Cobalt-mediated, enantioselective synthesis of C2 and C 1 dienes
AU - Boyd, W.
AU - Crimmin, Mark R.
AU - Rosebrugh, Lauren E.
AU - Schomaker, Jennifer M.
AU - Bergman, Robert G.
AU - Toste, F. Dean
PY - 2010/11/24
Y1 - 2010/11/24
N2 - The asymmetric C-H functionalization of norbornene and norbornadiene with five-, six-, and seven-membered cyclic enones mediated by the reactive intermediate [{η5-(tBuMe2Si)C 5H4}Co(NO)2] is reported. A novel base mixture derived from enantiopure ammonium salts and NaHMDS was used as a source of chirality, and this enantioselective desymmetrization of Cs alkenes has been applied to the asymmetric synthesis of C2- and C 1-symmetric diene ligands in high regioselectivity (3.7-20:1 anti/syn), near perfect diastereoselectivity (>99:1 dr), and high enantioselectivity (90-96% ee). © 2010 American Chemical Society.
AB - The asymmetric C-H functionalization of norbornene and norbornadiene with five-, six-, and seven-membered cyclic enones mediated by the reactive intermediate [{η5-(tBuMe2Si)C 5H4}Co(NO)2] is reported. A novel base mixture derived from enantiopure ammonium salts and NaHMDS was used as a source of chirality, and this enantioselective desymmetrization of Cs alkenes has been applied to the asymmetric synthesis of C2- and C 1-symmetric diene ligands in high regioselectivity (3.7-20:1 anti/syn), near perfect diastereoselectivity (>99:1 dr), and high enantioselectivity (90-96% ee). © 2010 American Chemical Society.
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U2 - 10.1021/ja107968c
DO - 10.1021/ja107968c
M3 - Article
C2 - 21033667
SN - 0002-7863
VL - 132
SP - 16365
EP - 16367
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
IS - 46
ER -