911224-87-8Relevant academic research and scientific papers
Rhodium-catalyzed asymmetric addition of arylboronic acids to β-phthaliminoacrylate esters toward the synthesis of β-amino acids
Nishimura, Takahiro,Wang, Jun,Nagaosa, Makoto,Okamoto, Kazuhiro,Shintani, Ryo,Kwong, Fuk-Yee,Yu, Wing-Yiu,Chan, Albert S. C.,Hayashi, Tamio
supporting information; experimental part, p. 464 - 465 (2010/03/25)
(Chemical Equation Presented) Rhodium-catalyzed asymmetric 1,4-addition of arylboronic acids to β-phthaliminoacrylate esters took place efficiently to give high yields of β-aryl-β-amino acid esters with 96-99% enantioselectivity, which was realized by use of a hydroxorhodium/chiral diene complex. Copyright
Homochiral lithium amides for the asymmetric synthesis of β-amino acids
Davies, Stephen G.,Garrido, Narciso M.,Kruchinin, Dennis,Ichihara, Osamu,Kotchie, Luke J.,Price, Paul D.,Mortimer, Anne J. Price,Russell, Angela J.,Smith, Andrew D.
, p. 1793 - 1811 (2007/10/03)
Secondary homochiral lithium amides derived from α-methylbenzylamine undergo highly diastereoselective conjugate additions to a range of α,β-unsaturated esters. The corresponding β-amino acids are readily liberated by successive N-debenzylation and ester hydrolysis, furnishing (R)-β-amino butyric acid, (R)-β-amino pentanoic acid, (S)-β-leucine, (R)-β-amino octanoic acid, (S)-β-phenylalanine, (S)-β-tyrosine methyl ether, (S)-β-tyrosine hydrochloride and (S)-β-(2-methoxyphenyl)-β-amino propanoic acid in high yields and high ee. The application of this procedure to the synthesis of the natural products (R)-β-DOPA and (R)-β-lysine is demonstrated. The development of a simplified one-pot reaction protocol applicable to the multi-gram scale synthesis of homochiral β-amino esters is also delineated.
