500137-54-2Relevant academic research and scientific papers
Selective synthesis of either enantiomer of α-amino acids by switching the regiochemistry of the tricyclic iminolactones prepared from a single chiral source
Xu, Peng-Fei,Lu, Ta-Jung
, p. 658 - 661 (2003)
Preparation of L-α-amino acids was easily accomplished simply by exchanging the position of the lactone group of our recently reported chiral template I from C2 to C3. The new chiral template 7 was prepared in 54% overall yield over five steps from (1R)-(+)-camphor. Alkylation of iminolactone 7 afforded the α-monosubstituted products in good yields and excellent diastereoselectivities (>98%). Hydrolysis of the alkylated iminolactones furnished the desired L-α-amino acids in good yields and ee with nearly quantitative recovery of chiral auxiliary 4.
Asymmetric synthesis of α,α-disubstituted α-amino acids by diastereoselective alkylation of camphor-based tricyclic iminolactone
Xu, Peng-Fei,Li, Shuo,Lu, Ta-Jung,Wu, Chen-Chang,Fan, Botao,Golfis, Georgia
, p. 4364 - 4373 (2007/10/03)
A novel and convenient route for the preparation of chiral tricyclic iminolactones 9 and 10 from camphorquinone has been developed. Alkylation of iminolactones 9 and 10 provided iminolactones 16 and 17 in high yields which were, in turn, alkylated again t
