Umpolung Synthesis of Vicinal Diamines: Diastereoselective Addition of 2‑Azaallyl Anions to Davis–Ellman’s Imines
Leleti Rajender Reddy
Sharadsrikar Kotturi
Rajesh Shenoy
Kumara Swamy Nalivela
Chirag Patel
Poojabahen Raval
Vinkal Zalavadiya
10.1021/acs.orglett.8b02331.s001
https://acs.figshare.com/articles/journal_contribution/Umpolung_Synthesis_of_Vicinal_Diamines_Diastereoselective_Addition_of_2_Azaallyl_Anions_to_Davis_Ellman_s_Imines/6974108
A highly
regioselective and diastereoselective addition of 2-azaallyl
anions to <i>N</i>-<i>tert</i>-butanesulfinylimines
is reported. This methodology affords the preparation of enantiomerically
and diastereomerically pure vicinal diamines bearing two adjacent
stereocenters. Reactions proceed efficiently (yield up to 94%), diastereoselectively
(<i>dr</i> values up to 98:2:0:0), and site-selectively
to deliver products with differentiated amino groups.
2018-08-16 12:20:18
butanesulfinylimine
Diastereoselective Addition
Imine
Vicinal Diamines
dr values
regioselective
methodology
enantiomerically
stereocenter
Anion
Azaallyl
diastereoselective addition
Umpolung Synthesis
Davis
vicinal diamines
2- azaallyl anions
diastereomerically
preparation
site-selectively
diastereoselectively
tert