ISSN:
0899-0042
Keywords:
2,3-epoxyalcohols
;
enantiomeric elution order
;
protective groups
;
chain length influence
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
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 OSitBuPh2) 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.
Additional Material:
1 Ill.
Type of Medium:
Electronic Resource
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