147780-61-8Relevant articles and documents
Synthesis of chiral N-phosphinyl α-imino esters and their application in asymmetric synthesis of α-amino esters by reduction
Xiong, Yiwen,Mei, Haibo,Wu, Lingmin,Han, Jianlin,Pan, Yi,Li, Guigen
, p. 653 - 659 (2014)
A variety of chiral N-phosphinyl a-imino esters have been synthesized for the first time from ketoesters and phosphinylamide, which were then reduced by L-selectride to give the corresponding N-phosphinyl-protected a-amino esters. The reduction proceeded very well with excellent chemical yields (88-98%) as well as high diastereoselectivities (96:4 to 99:1). Some of these products could be obtained without column chromatography and recrystallization. The chiral phosphinyl auxiliary could be easily cleaved under acidic conditions.
Direct ortho -Selective C-H Functionalization of Carboxybenzyl-Protected Arylalkylamines via Ir(III)-Catalyzed C-H Activation
Li, Guobao,Hu, Jundie,Zeng, Runsheng,Shi, Da-Qing,Zhao, Yingsheng
supporting information, p. 2454 - 2458 (2018/04/26)
A convenient and practical approach to synthesize ortho-alkynylated arylalkylamines through ortho-selective C-H functionalization has been developed using Cbz-amide as the directing group and Ir(III) as the catalyst. Various substrates were well tolerated, affording the corresponding products in moderate to good yields. Moreover, preliminary mechanistic study revealed the role of the amide as the coordination center to cooperate with the Ir(III) complex during C-H activation. Development of this Cbz-amide-promoted CAr-H functionalization offers a practical approach with potential applications in organic synthesis.
Formation of Non-Natural α,α-Disubstituted Amino Esters via Catalytic Michael Addition
Teegardin, Kip A.,Gotcher, Lacey,Weaver, Jimmie D.
supporting information, p. 7239 - 7244 (2018/11/25)
The enolate monoanion of amino esters is explored, and the first catalytic Michael addition of α-amino esters is demonstrated. These studies indicate that the acidity of the αC-H is the primary factor determining reactivity. Thus, polyfluorophenylglycine amino esters yield novel α-amino esters in the presence of a catalytic amount of a guanidine-derived base and Michael acceptors. Reactivity requires an acidic N-H, which is accomplished using common protecting groups such as N-Bz, N-Boc, and N-Cbz. Calculations and labeling experiments provide insight into the governing principles in which a key C-to-N proton transfer occurs, resulting in an expansion of the scope to include a number of natural amino esters. The study culminates with a late-stage functionalization of peptidic γ-secretase inhibitor, DAPT.
