173723-62-1Relevant articles and documents
Stereodivergent Synthesis of Carbocyclic Quaternary α-Amino Acid Derivatives Containing Two Contiguous Stereocenters
Bai, Tian,Dong, Xiu-Qin,Fu, Cong,He, Ling,Wang, Chun-Jiang,Xiao, Lu,Xiong, Qi,Zhang, Zongpeng
supporting information, (2022/02/23)
A novel approach to stereodivergent synthesis of carbocyclic α-quaternary amino acid derivatives, bearing two contiguous stereocenters, is proposed through sequential dual Cu/Ir-catalyzed asymmetric allylation and ring-closing metathesis. A variety of five and six-membered carbocyclic α-quaternary amino acid derivatives could be readily achieved in good to high yields with exclusive regioselectivities, excellent diastereoselectivities (13: 1- > 20: 1 dr) and enantioselectivities (generally >99% ee). Of particular note is that the current protocol is also a versatile synthetic tool for the stereodivergent construction of the challenging seven and eight-membered carbocyclic α-amino acid derivatives. All four stereoisomers of these important molecules could be precisely synthesized through the permutation of chiral Cu/Ir catalytic system. The power of this strategy has been demonstrated for the facile access to some biologically active chiral molecules, such as spiro-hydantoins.
Solid-phase synthesis of peptide thioureas and thiazole-containing macrocycles through ru-catalyzed ring-closing metathesis
Cohrt, A. Emil,Nielsen, Thomas E.
supporting information, p. 71 - 77 (2014/03/21)
N-Terminally modified α-thiourea peptides can selectively be synthesized on solid support under mild reaction conditions using N,N′-di-Boc-thiourea and Mukaiyama's reagent (2-chloro-1-methyl-pyridinium iodide). This N-terminal modification applies to the 20 proteinogenic amino acid residues on three commonly used resins for solid-phase synthesis. Complementary methods for the synthesis of α-guanidino peptides have also been developed. The thiourea products underwent quantitative reactions with α-halo ketones to form thiazoles in excellent purities and yields. When strategically installed between two alkene moieties, said thiazole core was conveniently embedded in peptide macrocycles via Ru-catalyzed ring-closing metathesis reactions. Various 15-17 membered macrocycles were easily accessible in all diastereomeric forms using this methodology. The developed "build/couple/pair" strategy is well suited for the generation of larger and stereochemically complete screening libraries of thiazole-containing peptide macrocycles.
Gold-catalyzed cycloisomerizations of ene-ynamides
Couty, Sylvain,Meyer, Christophe,Cossy, Janine
experimental part, p. 1809 - 1832 (2009/06/28)
The gold-catalyzed cycloisomerizations of 1,6-ene-ynamides proceed under mild conditions and lead to cyclobutanones from terminal or trimethylsilyl substituted ynamides, or to carbonyl compounds bearing a 2,3-methanopyrrolidine subunit from substrates pos
