Asymmetric Induction on Copper(I) Chloride catalyzed 1,4‐addition of alkylmagnesium chlorides to α, β‐disubstituted ( E )‐enoylsultams and subsequent protonation | Zendy

Oppolzer Wolfgang | Zendy; Kingma Arend J. | Zendy

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Asymmetric Induction on Copper(I) Chloride catalyzed 1,4‐addition of alkylmagnesium chlorides to α, β‐disubstituted ( E )‐enoylsultams and subsequent protonation

Author(s) -

Oppolzer Wolfgang,

Kingma Arend J.

Publication year - 1989

Publication title -

helvetica chimica acta

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.74

H-Index - 82

eISSN - 1522-2675

pISSN - 0018-019X

DOI - 10.1002/hlca.19890720622

Subject(s) - chemistry , stereocenter , reagent , protonation , alkyl , asymmetric induction , medicinal chemistry , copper , catalysis , chloride , cleavage (geology) , conjugated system , grignard reagent , organic chemistry , enantioselective synthesis , ion , engineering , polymer , geotechnical engineering , fracture (geology)

Successive treatment of conjugated N ‐enoylsultams 2 with alkyl Grignard reagents/CuCl and aq. NH 4 Cl solution generated selectively two stereogenic centers at C(α) and C(β) providing, after flash chromatography and crystallization, acylsultams 5 in high purity. Mild cleavage afforded the recovered sultam auxiliary 1 and enantiomerically pure carboxylic acids 7 .

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