Premium
Absolute Configuration Determination and Convenient Asymmetric Synthesis of cis ‐3‐(9‐Anthryl)cyclohexanol with Proline as a Catalyst
Author(s) -
Wysocki Jędrzej,
Kwit Marcin,
Gawronski Jacek
Publication year - 2012
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.22079
Subject(s) - chemistry , absolute configuration , cyclohexanol , circular dichroism , chirality (physics) , cyclohexanone , catalysis , enantioselective synthesis , derivative (finance) , proline , stereocenter , stereochemistry , crystallography , computational chemistry , organic chemistry , biochemistry , chiral symmetry breaking , physics , amino acid , quantum mechanics , financial economics , nambu–jona lasinio model , economics , quark
cis ‐(3 R )‐(9‐anthryl) derivative of cyclohexanol was conveniently obtained in enantiomerically pure form from 2‐cyclohexenone using asymmetric Michael addition of anthrone catalyzed by l ‐proline in a key step. The absolute configuration of the addition product was unequivocally determined by means of electronic circular dichroism measurements combined with calculation of the circular dichroism spectrum by using a density functional theory method. Chirality 24:833–839, 2012 . © 2012 Wiley Periodicals, Inc.