240420-23-9Relevant articles and documents
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 (2002)
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.
The synthesis of novel amino acids via hydroboration-suzuki cross coupling
Campbell, Andrew D.,Raynham, Tony M.,Taylor, Richard J. K.
, p. 5263 - 5266 (2007/10/03)
The Gamer aldehyde-derived methylene alkene has been hydroborated using 9-BBN and the resulting organoborane employed in palladium-catalysed Suzuki coupling reactions to produce, after hydrolysis-oxidation, a range of novel amino acids as their N-BOC protected derivatives.
