Enantioselective synthesis of trans-aryl- and -heteroaryl-substituted cyclopropylboronates by copper(I)-catalyzed reactions of allylic phosphates with a diboron derivative.
A new asymmetric route for the synthesis of trans-2-aryl- and -heteroaryl-substituted cyclopropylboronates has been developed. (Z)-3-arylallylic phosphates were converted to the optically active products with high yield and diastereo- and enantioselectivity through a copper(I)-catalyzed reaction with a diboron derivative. Under mild reaction conditions, the reaction affords the arylcyclopropane products with a functional group and a heteroaromatic group in a highly enantioselective manner. When (E)-allylic phosphates were used as substrates, a ligand-controlled product switch between the trans and cis configurations was observed.
Zhong
Chongmin
C
Department of Chemistry, Faculty of Science, Hokkaido University, Sapporo 060-0810, Japan.
Kunii
Shun
S
Kosaka
Yuki
Y
Sawamura
Masaya
M
Ito
Hajime
H
D000498:Allyl Compounds / Q000737:chemistry*; D001896:Boron Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D003521:Cyclopropanes / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010755:Organophosphates / Q000737:chemistry*; D013237:Stereoisomerism
D000498:Allyl Compounds; D001896:Boron Compounds; D003521:Cyclopropanes; D010755:Organophosphates; D003300:Copper