220854-79-5Relevant academic research and scientific papers
Enantioselective synthesis of (2-pyridyl)alanines via catalytic hydrogenation and application to the synthesis of L-azatyrosine.
Adamczyk,Akireddy,Reddy
, p. 3157 - 3159 (2001)
[reaction: see text] A novel method for the synthesis of (2-pyridyl)alanines 2a-b was developed by converting (2-pyridyl)dehydroamino acid derivatives 1a-b to the corresponding N-oxides 3a-b followed by asymmetric hydrogenation using (R,R)-[Rh(Et-DUPHOS)(
Stereoselective Synthesis of (E)-α,β-dehydroamino acid esters
Yasuno, Yoko,Hamada, Makoto,Yamada, Takeshi,Shinada, Tetsuro,Ohfune, Yasufumi
supporting information, p. 1884 - 1888 (2013/05/08)
Dehydroamino acid (Dhaa) is recognized as a useful tool or substrate for amino acid and peptide research. Although the stereoselective synthesis of the thermodynamically more stable Z-Dhaa has been well examined and established, the stereoselective synthesis of E-Dhaa has still remained to be a challenging synthetic task. In this paper, a stereoselective synthesis of E-Dhaa esters using a new (α-diphenylphosphono)glycine is described. The characteristic aspects of the new method are summarized as follows: (i) metal additives play an important role in the promotion of E-stereoselectivities. (ii) the use of NaI was effected for the synthesis of E-Dhaas bearing an aryl substituent and an amino functionality, (iii) MgBr2·OEt2 and ZnCl 2 contributed to improve the E-stereoselective synthesis of E-Dhaas bearing an alkyl substituent and an oxygen functionality, (iv) various protecting and functional groups were compatible under the reaction conditions, and (v) N-Cbz, Boc, and acyl-α-(diphenylphosphono)glycines were served for the stereoselective olefination reaction to provide the corresponding E-Dhaas. A variety of (E)-dehydroamino acid esters were stereoselectively synthesized by using (diphenylphosphono)glycinate. The stereoselectivity was influenced by metal additives. Various (E)-dehydroamino acid esters were prepared by the condensation reaction of the new phosphonates with easily available aldehydes by choosing the appropriate reaction conditions.
Preparation of (S)-2-quinolylalanine by asymmetric hydrogenation
Jones,Palmer,Paul,Tiffin
, p. 1211 - 1214 (2007/10/03)
The synthesis of (S)-2-quinolylalanine through asymmetric hydrogenation with (S,S)-Et-DuPHOS-Rh is described. The reaction has been extended to other 2-pyridylalanine derivatives.
