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Influence of the nature and substitution of chiral 2,3‐epoxy alcohol derivatives on the enantiomeric elution order on chiralcel OD column
Author(s) -
Nacro Kassoum,
Zedde Chantal,
Escudier JeanMarc,
Baltas Michel,
Gorrichon Liliane,
Neier Reinhard
Publication year - 1998
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/(sici)1520-636x(1998)10:9<804::aid-chir5>3.0.co;2-o
Subject(s) - chemistry , enantiomer , nerol , elution , epoxide , chirality (physics) , alkoxy group , alcohol , epoxy , enantioselective synthesis , enantiomeric excess , chromatography , stereochemistry , organic chemistry , geraniol , catalysis , alkyl , nambu–jona lasinio model , chiral symmetry breaking , physics , quantum mechanics , essential oil , quark
A number of 2,3‐epoxy alcohol derivatives (1–16), obtained either as racemates or through the Sharpless asymmetric epoxidation reaction, were studied on a Chiralcel OD column. Nearly all compounds exhibit good enantioselective resolution on this chiral support. The order of elution of enantiomers is reversed between nerol and geraniol compounds. For 2,3‐epoxy alcohols bearing a remote alkoxy (or silyloxy) group, the order of the enantiomeric elution alternates with the number n (n = 1–3) of methylenic groups present between the epoxide ring and the terminal OR (R = p − BrBn or OSitBuPh 2 ) functionality. In the case of trans 2,3‐epoxy alcohols for the same number n, the order of elution is reversed when changing the terminal group −OSi to −OR. The latter group greatly improves the separation of the two enantiomers. Chirality 10:804–807, 1998. © 1998 Wiley‐Liss, Inc.