Asymmetric synthesis of O-protected acyloins using enoate reductases: Stereochemical control through protecting group modification
O-Protected cyclic acyloins were obtained in nonracemic form through asymmetric bioreduction of α,β-unsaturated alkoxy ketones by using 11 different enoate reductases from the "Old Yellow Enzyme" family. The stereochemical outcome of the biotransformation could be switched by variation of the O-protecting group or by the ring size of the substrate, which allows access to both stereoisomers in up to >97 % ee Whereas α-alkoxy enones were readily accepted as substrates, β-analogs were not converted. Overall, α-alkoxy enones represent a novel type of substrate for flavin-dependent ene-reductases. Copyright
Winkler, Christoph K.,Stueckler, Clemens,Mueller, Nicole J.,Pressnitz, Desiree,Faber, Kurt
supporting information; experimental part
p. 6354 - 6358
(2011/02/24)
RADICAL CYCLIZATIONS OF DIOSPHENOL ω-HALOALKYL ETHERS TO OXABICYCLOALKANONES
Radical cyclization of diosphenol ω-haloalkyl ethers gives spiro- and fused oxabicycloalkanones.
Ponaras, Anthony A.,Zaim, Oemer
p. 2879 - 2882
(2007/10/02)
SYNTHESIS OF DIOSPHENOL ETHERS BY MEANS OF ALKOXYTRIMETHYLSILANES
α-Diketones may be O-alkylated with a variety of alkoxytrimethylsilanes.
Ponaras, A. A.,Meah, Md. Younus
p. 4953 - 4956
(2007/10/02)
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