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Cyclic Model for the Asymmetric Conjugate Addition of Organolithiums with EnoatesCyclic Model for the Asymmetric Conjugate Addition of Organolithiums with EnoatesAA00855740 |
"/Nishimura, Katsumi/"Nishimura, Katsumi ,
"/Fukuyama, Naoshi/"Fukuyama, Naoshi ,
"/Yamashita, Mitsuaki/"Yamashita, Mitsuaki ,
"/Sumiyoshi, Takaaki/"Sumiyoshi, Takaaki ,
"/Yamamoto, Yasutomo/"Yamamoto, Yasutomo ,
"/Yamada, Ken-ichi/"Yamada, Ken-ichi ,
"/Tomioka, Kiyoshi/"Tomioka, Kiyoshi
47
(
15
)
, pp.2256
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2264 , 2015-07-21 , Thieme Publishing Group
ISSN:0039-7881
NCID:AA00855740
Description
The chiral diether ligand controlled asymmetric conjugate addition of organolithiums to nona-2, 7-dienedioates preferentially proceeds via the s-cis conformation with coordination of the carbonyl oxygen atom to the lithium to give a lithium E-enolate intermediate. Subsequent intramolecular conjugate addition of the enolate also proceeds via a cyclic transition state involving the lithium and the s-cis-enoate, resulting in trans, trans-trisubstituted cyclohexanes with high enantiomeric excesses and yields.
Full-Text
http://repository.kulib.kyoto-u.ac.jp/dspace/bitstream/2433/202033/1/s-0034-1380702.pdf