Open AccessReinvestigation of a Catalytic, Enantioselective Alkene Dibromination and Chlorohydroxylation
Author(s) -
Scott E. Denmark,
Nessa Carson
Publication year - 2015
Publication title -
organic letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/acs.orglett.5b02650
Subject(s) - enantioselective synthesis , alkene , chemistry , enantiomer , chiral stationary phase , reagent , high performance liquid chromatography , catalysis , fidelity , organic chemistry , combinatorial chemistry , electrical engineering , engineering
Attempts to reproduce eight, putative, enantioselective dibromination and chlorohydroxylation reactions from oft-cited literature studies are described. The reactions were performed with full fidelity to the original report wherever possible. Analysis of the enantiomeric composition was performed by chiral stationary phase HPLC or SFC (CSP-HPLC or CSP-SFC), as opposed to the original report, which used chiral shift reagent NMR spectroscopy. After careful study, the reported levels of enantioselectivity were found to be incorrect. Possible explanations for the false positive results are discussed.