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Copper(I)‐Catalyzed Highly Enantioselective [3+3]‐Cycloaddition of β‐Aryl/Alkyl Vinyl Diazoacetates with Nitrones
Author(s) -
Zheng Haifeng,
Faghihi Isa,
Doyle Michael P.
Publication year - 2021
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.202100081
Subject(s) - chemistry , cycloaddition , catalysis , aryl , enantioselective synthesis , alkyl , yield (engineering) , copper , cyclopropene , medicinal chemistry , ligand (biochemistry) , organic chemistry , combinatorial chemistry , biochemistry , materials science , receptor , metallurgy
β‐Aryl/alkyl vinyl diazoacetates were investigated in metallo‐vinylcarbene reactions with nitrones, revealing a Rh 2 (OAc) 4 ‐catalyzed cyclopropene dimerization reaction and a copper(I) catalyzed [3+3]‐cycloaddition of nitrones. The chiral cyclopropyl‐In‐SaBox ligand with copper(I) catalysis could realize the asymmetric version of the cycloaddition reaction, delivering various 3,6‐dihydro‐1,2‐oxazine derivatives in good yield and with excellent enantioselectivity under mild conditions.