Carbamoyl Anion Addition to N-Sulfinyl Imines: Highly Diastereoselective Synthesis of α-Amino Amides
Journal of the American Chemical Society2013Vol. 135(15), pp. 5565–5568
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Jonathan T. Reeves, Zhulin Tan, Melissa A. Herbage, Zhengxu S. Han, Maurice A. Marsini, Zhibin Li, Guisheng Li, Yibo Xu, Keith R. Fandrick, Nina C. Gonnella, Scot Campbell, Shengli Ma, Nelu Grinberg, Hee‐Won Lee, Bruce Z. Lu, Chris H. Senanayake
Abstract
Carbamoyl anions, generated from N,N-disubstituted formamides and lithium diisopropylamide, add with high diastereoselectivity to chiral N-sulfinyl aldimines and ketimines to provide α-amino amides. The methodology enables the direct introduction of a carbonyl group without the requirement of unmasking steps as with other nucleophiles. The products may be converted to α-amino esters or 1,2-diamines. Iterative application of the reaction enabled the stereoselective synthesis of a dipeptide. Spectroscopic and computational studies support an anion structure with η(2) coordination of lithium by the carbonyl group.
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