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Asymmetric synthesis of 2,4,5-trisubstituted ?2-thiazolines.

ABSTRACT: ?(2)-Thiazolines are interesting heterocycles that display a wide variety of biological characteristics. They are also common in chiral ligands used for asymmetric syntheses and as synthetic intermediates. Herein, we present asymmetric routes to 2,4,5-trisubstituted ?(2)-thiazolines. These ?(2)-thiazolines were synthesized from readily accessible/commercially available ?,?-unsaturated methyl esters through a Sharpless asymmetric dihydroxylation and an O?N acyl migration reaction as key steps. The final products were obtained in good yields with up to 97?% enantiomeric excess.

SUBMITTER: Bengtsson C

PROVIDER: S-EPMC3784040 | biostudies-literature | 2013 Jul

REPOSITORIES: biostudies-literature

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Asymmetric synthesis of 2,4,5-trisubstituted Δ2-thiazolines.

Bengtsson Christoffer C Nelander Hanna H Almqvist Fredrik F

Chemistry (Weinheim an der Bergstrasse, Germany) 20130617 30

Δ(2)-Thiazolines are interesting heterocycles that display a wide variety of biological characteristics. They are also common in chiral ligands used for asymmetric syntheses and as synthetic intermediates. Herein, we present asymmetric routes to 2,4,5-trisubstituted Δ(2)-thiazolines. These Δ(2)-thiazolines were synthesized from readily accessible/commercially available α,β-unsaturated methyl esters through a Sharpless asymmetric dihydroxylation and an O→N acyl migration reaction as key steps. Th ...[more]

PMID: 23776083

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