Addressing the Configuration Stability of Lithiated Secondary Benzylic Carbamates for the Development of a Noncryogenic Stereospecific Boronate Rearrangement
详细信息 查看全文
- 作者：Keith R. Fandrick ; Nitinchandra D. Patel ; Jason A. Mulder ; Joe Gao ; Michael Konrad ; Elizabeth Archer ; Frederic G. Buono ; Adil Duran ; Rolf Schmid ; Juergen Daeubler ; Daniel R. Fandrick ; Shengli Ma ; Nelu Grinberg ; Heewon Lee ; Carl A. Busacca ; Jinhua J. Song ; Nathan K. Yee ; Chris H. Senanayake
- 刊名：Organic Letters
- 出版年：2014
- 出版时间：September 5, 2014
- 年：2014
- 卷：16
- 期：17
- 页码：4360-4363
- 全文大小：383K
- ISSN：1523-7052
文摘
A practical noncryogenic process for the Aggarwal stereospecific boronate rearrangement with chiral secondary benzylic carbamates has been developed. The use of LDA instead of sec-BuLi combined with an in situ trapping of the unstable lithiated carbamate was critical to success. Furthermore, this new process increased the substrate scope to include the versatile aryl iodide and bromide substrates. The methodology was applied to a diverse array of substrates and was demonstrated on multikilogram scale.