One pot 'click' reactions: tandem enantioselective biocatalytic epoxide ring opening and [3+2] azide alkyne cycloaddition

Halohydrin dehalogenase (HheC) can perform enantioselective azidolysis of aromatic epoxides to 1,2-azido alcohols which are subsequently ligated to alkynes producing chiral hydroxy triazoles in a one-pot procedure with excellent enantiomeric excess.

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2010-01, Vol.46 (6), p.898-900
Main Authors: Campbell-Verduyn, Lachlan S, Szymański, Wiktor, Postema, Christiaan P, Dierckx, Rudi A, Elsinga, Philip H, Janssen, Dick B, Feringa, Ben L
Format: Article
Language:English
Subjects:
Alkynes - chemistry
Azides - chemistry
Biocatalysis
Epoxy Compounds - chemistry
Hydrolases - chemistry
Hydrolases - metabolism
Stereoisomerism
Triazoles - chemical synthesis
Triazoles - chemistry
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Summary:Halohydrin dehalogenase (HheC) can perform enantioselective azidolysis of aromatic epoxides to 1,2-azido alcohols which are subsequently ligated to alkynes producing chiral hydroxy triazoles in a one-pot procedure with excellent enantiomeric excess.
ISSN:1359-7345
1364-548X
DOI:10.1039/b919434g