Umpolung Synthesis of Vicinal Diamines: Diastereoselective Addition of 2‑Azaallyl Anions to Davis–Ellman’s Imines
- Leleti Rajender Reddy (2062720)
- Sharadsrikar Kotturi (5339978)
- Rajesh Shenoy (5339981)
- Kumara Swamy Nalivela (5637422)
- Chirag Patel (263840)
- Poojabahen Raval (5637425)
- Vinkal Zalavadiya (5637428)
Publication date
August 2018
DOI Publisher
American Chemical Society (ACS)Abstract
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
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