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Immobilization of cis ‐4‐Hydroxydiphenylprolinol Silyl Ethers onto Polystyrene. Application in the Catalytic Enantioselective Synthesis of 5‐Hydroxyisoxazolidines in Batch and Flow
Author(s) -
Lai Junshan,
Sayalero Sonia,
Ferrali Alessandro,
OsorioPlanes Laura,
Bravo Fernando,
RodríguezEscrich Carles,
Pericàs Miquel A.
Publication year - 2018
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201800572
Subject(s) - chemistry , enantioselective synthesis , silylation , diastereomer , catalysis , polystyrene , yield (engineering) , tandem , organic chemistry , polymer , polymer chemistry , combinatorial chemistry , materials science , composite material , metallurgy
A new family of polystyrene‐supported cis ‐4‐hydroxydiphenylprolinol silyl ethers has been prepared, and the resulting polymers have been evaluated as organocatalysts to promote the tandem reaction between N ‐protected hydroxylamines and α,β‐unsaturated aldehydes in batch and flow. The new PS‐supported catalysts compare favorably with well‐established immobilized Jørgensen‐Hayashi catalysts, affording 5‐hydroxyisoxazolidines as single diastereoisomers with high enantioselectivities and good yields (up to 83% yield, up to 99% ee).