Influences of catalyst configuration and catalyst loading on selectivities in reactions of diazoacetamides. Barrier to equilibrium between diastereomeric conformations.
[reaction: see text] Stereoelectronic factors present a barrier to equilibrium between diastereomeric conformations resulting in differences in selectivity as a function of catalyst configuration. The bis(trimethylsilyl)-methyl protective group is inert to insertion but directs carbon-hydrogen insertion with enhanced enantiocontrol.
Doyle
Michael P
MP
Department of Chemistry, University of Arizona, Tucson, Arizona 85721, USA. mdoyle@u.arizona.edu
Hu
Wenhao
W
Wee
Andrew G H
AG
Wang
Zhongyi
Z
Duncan
Sammy C
SC
D002384:Catalysis; D003979:Diazonium Compounds / Q000737:chemistry*; D013237:Stereoisomerism
D003979:Diazonium Compounds; C011752:diazoacetamide