Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 140, Issue 23, Pages 7052-7055Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.8b02992
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Funding
- Netherlands Organization for Scientific Research (NWO-CW)
- Royal Netherland Academy of Arts and Sciences (KNAW)
- Ministry of Education Culture and Science [024.601035]
- A*STAR (NSS)
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The highly regio- and enantioselective (up to >99:1 dr, up to 99:1 er) desymmetrization of meso-1,4-dibromocycloalk-2-enes using asymmetric allylic substitution with organolithium reagents to afford enantioenriched bromocycloalkenes (ring size of 5 to 7) has been achieved. The cycloheptene products undergo an unusual ring contraction. The synthetic versatility of this Cu(I)-catalyzed reaction is demonstrated by the concise stereocontrolled preparation of cyclic amino alcohols, which are privileged chiral structures in natural products and pharmaceuticals and widely used in synthesis and catalysis.
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