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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 .