Umpolung Synthesis of Vicinal Diamines: Diastereoselective Addition of 2‑Azaallyl Anions to Davis–Ellman’s Imines

Reddy, Leleti Rajender; Kotturi, Sharadsrikar; Shenoy, Rajesh; Nalivela, Kumara Swamy; Patel, Chirag; Raval, Poojabahen; Zalavadiya, Vinkal

doi:10.1021/acs.orglett.8b02331.s001

ol8b02331_si_001.pdf (7.28 MB)

Umpolung Synthesis of Vicinal Diamines: Diastereoselective Addition of 2‑Azaallyl Anions to Davis–Ellman’s Imines

journal contribution

posted on 2018-08-16, 12:20 authored by Leleti Rajender Reddy, Sharadsrikar Kotturi, Rajesh Shenoy, Kumara Swamy Nalivela, Chirag Patel, Poojabahen Raval, Vinkal Zalavadiya

A highly regioselective and diastereoselective addition of 2-azaallyl anions to N-tert-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 (dr values up to 98:2:0:0), and site-selectively to deliver products with differentiated amino groups.