271260-89-0Relevant academic research and scientific papers
Enantiomerically pure α-amino acid synthesis via hydroboration - Suzuki cross-coupling
Collier, Philip N.,Campbell, Andrew D.,Patel, Ian,Raynham, Tony M.,Taylor, Richard J. K.
, p. 1802 - 1815 (2007/10/03)
The Garner aldehyde-derived methylene alkene 5 and the corresponding benzyloxycarbonyl compound 25 undergo hydroboration with 9-BBN-H followed by palladium-catalyzed Suzuki coupling reactions with aryl and vinyl halides. After one-pot hydrolysis -oxidation, a range of known and novel nonproteinogenic amino acids were isolated as their N-protected derivatives. These novel organoborane homoalanine anion equivalents are generated and transformed under mild conditions and with wide functional group tolerance: electron-rich and -poor aromatic iodides and bromides (and a vinyl bromide) all undergo efficient Suzuki coupling. The extension of this methodology to prepare meso-DAP, R,R-DAP, and R,R-DAS is also described.
Synthesis of unnatural amino acids via suzuki cross-coupling of enantiopure vinyloxazolidine derivatives
Sabat, Mark,Johnson, Carl R.
, p. 1089 - 1091 (2007/10/03)
(R and S)-α-Amino alcohols and α-amino acids, including 4-methoxyhomophenylalanine, with a variety of unnatural side chains have been synthesized via palladium-catalyzed cross-coupling Suzuki reactions. The key building blocks 1 and 2, synthesized from the common achiral precursor 2-butene-1,4-diol, were made enantiopure utilizing a Pseudomonas cepacia lipase-catalyzed kinetic resolution. The optimal conditions for the Suzuki cross-coupling and the subsequent oxidations of the resultant α-amino alcohols are described.
