Expedient synthesis of chiral 1,2- and 1,4-diamines: protecting group dependent regioselectivity in direct organocatalytic asymmetric Mannich reactions.
[reaction: see text] Organocatalytic asymmetric Mannich reaction of protected amino ketones with imines in the presence of an L-proline-derived tetrazole catalyst afforded diamines with excellent yields and enantioselectivities of up to 99%. The amino ketone protecting group controlled the regioselectivity of the reaction providing access to chiral 1,2-diamines from azido ketones and 1,4-diamines from phthalimido ketones.
Chowdari
Naidu S
NS
The Skaggs Institute for Chemical Biology and the Department of Chemistry, The Scripps Research Institute, La Jolla, California 92037, USA.
Ahmad
Moballigh
M
Albertshofer
Klaus
K
Tanaka
Fujie
F
Barbas
Carlos F
CF
D001386:Azides / Q000737:chemistry; D002384:Catalysis; D003959:Diamines / Q000138:chemical synthesis* / Q000737:chemistry; D007097:Imines / Q000737:chemistry; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D011392:Proline / Q000737:chemistry*; D013237:Stereoisomerism; D013777:Tetrazoles / Q000737:chemistry
D001386:Azides; D003959:Diamines; D007097:Imines; D007659:Ketones; D013777:Tetrazoles; D011392:Proline