Synthesis of Novel Functionalized Polymers for the Diastereoselective Protonation of Chiral Enolates | Zendy

Mackenstedt Marc | Zendy; Krause Norbert | Zendy

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Synthesis of Novel Functionalized Polymers for the Diastereoselective Protonation of Chiral Enolates

Author(s) -

Mackenstedt Marc,

Krause Norbert

Publication year - 2004

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.200400429

Subject(s) - chemistry , protonation , enol , polymer , silylation , styrene , lithium (medication) , monomer , polymer chemistry , selectivity , polymerization , radical polymerization , organic chemistry , catalysis , copolymer , medicine , ion , endocrinology

The polymeric, chelating proton donors 7 and 8 were synthesized by radical polymerization of the monomers 5 / 6 with different amounts of styrene. Protonation of chiral lithium enolates derived from silyl enol ethers 9 gave cis / trans ratios of up to 94:6 ( 10a ) and 99:1 ( 10b ), respectively. The polymers can be recycled and used repeatedly without appreciable loss of selectivity. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

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