Asymmetric lithiation-substitution of amines involving rearrangement of borates.
Asymmetric lithiation of substituted benzylamines, N-Boc-pyrrolidine, or N-Boc-indoline using Beak's methodology was followed by electrophilic quench with trialkylboranes. The resulting borate intermediates rearrange with concomitant C-N bond breakage to give, after oxidation, chiral secondary alcohols with high enantioselectivity.
Coldham
Iain
I
Department of Chemistry, University of Sheffield, Sheffield S3 7HF, UK. i.coldham@sheffield.ac.uk
Patel
Jignesh J
JJ
Raimbault
Sophie
S
Whittaker
David T E
DT
Adams
Harry
H
Fang
Guang Y
GY
Aggarwal
Varinder K
VK
D000588:Amines / Q000737:chemistry*; D001881:Borates / Q000737:chemistry*; D002219:Carbamates / Q000737:chemistry; D018360:Crystallography, X-Ray; D008094:Lithium / Q000737:chemistry*; D008968:Molecular Conformation; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D010084:Oxidation-Reduction; D013034:Sparteine / Q000737:chemistry
D000588:Amines; D001881:Borates; D002219:Carbamates; D009942:Organometallic Compounds; D013034:Sparteine; D008094:Lithium