1416989-77-9Relevant articles and documents
A General Amino Acid Synthesis Enabled by Innate Radical Cross-Coupling
Ni, Shengyang,Garrido-Castro, Alberto F.,Merchant, Rohan R.,de Gruyter, Justine N.,Schmitt, Daniel C.,Mousseau, James J.,Gallego, Gary M.,Yang, Shouliang,Collins, Michael R.,Qiao, Jennifer X.,Yeung, Kap-Sun,Langley, David R.,Poss, Michael A.,Scola, Paul M.,Qin, Tian,Baran, Phil S.
, p. 14560 - 14565 (2018)
The direct union of primary, secondary, and tertiary carboxylic acids with a chiral glyoxylate-derived sulfinimine provides rapid access into a variety of enantiomerically pure α-amino acids (>85 examples). Characterized by operational simplicity, this radical-based reaction enables the modular assembly of exotic α-amino acids, including both unprecedented structures and those of established industrial value. The described method performs well in high-throughput library synthesis, and has already been implemented in three distinct medicinal chemistry campaigns.
Unnatural chiral N - Tert -butanesulfinyl α-amino acid synthesis; A general synthetic strategy to N -boc-phenylalanine analogue alternatives
Lin, Li,Fu, Xu,Ma, Xiaojuan,Zhang, Jinlong,Wang, Rui
supporting information, p. 2559 - 2563,5 (2012/12/11)
This work provides a general approach to unnatural chiral N-tert-butanesulfinyl α-amino acid synthesis with high yields and excellent diastereoselectivities (dr up to 98:2). The asymmetric addition of organometallic reagents to N-tert-butylsulfinyl imino acetate proceeded with excellent diastereo- and regioselectivities even on a 10 mmol scale. The sterically constrained 2,6-dimethyltyrosine (Dmt) derivative was also readily prepared from commercially available and inexpensive starting materials through simple steps.
