1429442-39-6Relevant articles and documents
Carbamoyl anion addition to N -sulfinyl imines: Highly diastereoselective synthesis of α-amino amides
Reeves, Jonathan T.,Tan, Zhulin,Herbage, Melissa A.,Han, Zhengxu S.,Marsini, Maurice A.,Li, Zhibin,Li, Guisheng,Xu, Yibo,Fandrick, Keith R.,Gonnella, Nina C.,Campbell, Scot,Ma, Shengli,Grinberg, Nelu,Lee, Heewon,Lu, Bruce Z.,Senanayake, Chris H.
, p. 5565 - 5568 (2013/05/22)
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 η2 coordination of lithium by the carbonyl group.
