Carbamoyl Anion Addition to N-Sulfinyl Imines: Highly Diastereoselective Synthesis of 伪-Amino Amides
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- 作者：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 ; Heewon Lee ; Bruce Z. Lu ; Chris H. Senanayake
- 刊名：The Journal of the American Chemical Society
- 出版年：2013
- 出版时间：April 17, 2013
- 年：2013
- 卷：135
- 期：15
- 页码：5565-5568
- 全文大小：367K
- 年卷期：v.135,no.15(April 17, 2013)
- ISSN：1520-5126
文摘
Carbamoyl anions, generated from N,N-disubstituted formamides and lithium diisopropylamide, add with high diastereoselectivity to chiral N-sulfinyl aldimines and ketimines to provide 伪-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 伪-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 畏2 coordination of lithium by the carbonyl group.