Enantioselective enzymatic desymmetrization of highly functionalized meso tetrahydropyranyl diols.
The enantioselective enzymatic desymmetrization of several highly substituted meso-tetrahydropyranyl diols is described. This transformation leads to valuable building blocks containing up to five stereogenic centers, which are revealed in a single step with both high yields and excellent enantiomeric excesses. Moreover, it was shown that this kind of building blocks could provide an easy access to both enantiomers of highly functionalized stereotetrads.
Candy
Mathieu
M
Aix-Marseille Université, Institut des Sciences Moléculaires de Marseille, iSm2 CNRS UMR6263-équipe STeRéO Campus Saint-Jérôme, 13397 Marseille Cedex 20, France.
Audran
Gérard
G
Bienaymé
Hugues
H
Bressy
Cyril
C
Pons
Jean-Marc
JM
D000438:Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D008049:Lipase / Q000378:metabolism*; D015394:Molecular Structure; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry; D020103:Rhizomucor / Q000201:enzymology*; D013237:Stereoisomerism
D000438:Alcohols; D011714:Pyrans; D008049:Lipase