Polymer supported enantioselective reactions. II. α-Methylation of cyclohexanone | Zendy

Colin R. McArthur | Zendy; Paul M. Worster | Zendy; Jilong Jiang | Zendy; Clifford C. Leznoff | Zendy

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Polymer supported enantioselective reactions. II. α-Methylation of cyclohexanone

Author(s) -

Colin R. McArthur,

Paul M. Worster,

Jilong Jiang,

Clifford C. Leznoff

Publication year - 1982

Publication title -

canadian journal of chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.323

H-Index - 68

eISSN - 1480-3291

pISSN - 0008-4042

DOI - 10.1139/v82-254

Subject(s) - chemistry , cyclohexanone , enantioselective synthesis , enantiomer , copolymer , styrene , selectivity , methylation , divinylbenzene , organic chemistry , enantiomeric excess , ether , polymer , polymer chemistry , catalysis , biochemistry , gene

Insoluble cross-linked copolymers of styrene and 1% divinylbenzene with covalently bonded (S)-2-aminoalkoxy groups were used in the enantioselective α-methylation of cyclohexanone through the corresponding imines. Enantiomeric excesses of 94% of (S)-2-methylcyclohexanone were observed on methylation at 20 °C. An analogous optically active 2-aminoalkyl benzyl ether, under otherwise identical conditions, resulted in a lower enantiomeric excess (49%) with selectivity approaching that of the polymer only at −78 °C.

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