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A versatile, enantioselective, stereocontrolled synthesis of (1S,2R)-imidazoleglycerol

โœ Scribed by Manuel M. Paz; Juan F. Cornea; M. Isabel Cabeza; F. Javier Sardina

Publisher
Elsevier Science
Year
1996
Tongue
French
Weight
297 KB
Volume
37
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

An efficient (21% overall yield), enantio-and diastereoselective. 11-step synthesis of (lS,2R)-imidazoleglycerol has been developed. The key steps are the stereoselective hydroxyiation of an acyloxazolidinone enolate, the alkylation of a thioester with (MOMOCHz)$uLi and the stereodivergent reduction of the resulting ketone. The scope of the reaction of the enolate derived from 10 with heteroatom electrophiles has been studied.

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โœ Jens Nieschalk; David O'Hagan ๐Ÿ“‚ Article ๐Ÿ“… 1997 ๐Ÿ› Elsevier Science ๐ŸŒ English โš– 350 KB

A straightforward three step route to (1S,2R)-and (1R,2R)-[2H]-glycerols la and lb is reported. The key asymmetric step involves an AD-mix-l~ dihydroxylation on deuterium labelled Z-and E-allyl benzoates 4a and 4b. The route should facilitate the use of [2H]-glycerols la-ld in high enantiomeric puri