Premium
Catalytic Enantioselective Synthesis of Halocyclopropanes
Author(s) -
Pons Amandine,
Ivashkin Pavel,
Poisson Thomas,
Charette André B.,
Pannecoucke Xavier,
Jubault Philippe
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201600649
Subject(s) - enantioselective synthesis , carbenoid , cyclopropanation , catalysis , rhodium , ethyl diazoacetate , enantiomer , enantiomeric excess , combinatorial chemistry , chemistry , chirality (physics) , organic chemistry , physics , chiral symmetry , quantum mechanics , quark , nambu–jona lasinio model
A catalytic asymmetric synthesis of halocyclopropanes is described. The developed method is based on a carbenoid cyclopropanation of 2‐haloalkenes with tert ‐butyl α‐cyano‐α‐diazoacetate using a chiral rhodium catalyst that permits access to a broad range of highly functionalized chiral halocyclopropanes (F, Cl, Br, and I) in good yields, moderate diastereoselectivity, and excellent enantiomeric ratios. The reported methodology represents the first general catalytic enantioselective approach to halocyclopropanes.