141209-95-2Relevant articles and documents
Asymmetric synthesis of non-natural amino acid derivatives: (2R/3S) and (2S/3R) 2-(tert-butoxycarbonylamino)-3-cyclohexyl-3-phenyl propanoic acids
Yang, Rui,Guo, Ya-Fei,Gao, Zhan-Yong,Zhao, Qian,Zhang, Qian-Yang,Lin, Jun
, p. 86 - 89 (2015)
Highly conformationally-constrained novel α-amino acid derivatives ((2R/3S ) and (2S/3R )-2-(tert-butoxycarbonylamino)-3- cyclohexyl-3-phenylpropanoic acids) have been synthesised with high stereoselectivity (> 90% de) and in 36-37% overall yields. In the synthesis, Evans' auxiliary (4(R/S )-4-phenyl-oxzaolidin-2-one) was used to control the stereoselectivity via the key reactions of asymmetric Michael addition, azidation and catalytic hydrogenolysis.
Conjugate addition of aryl nucleophiles to α,β-unsaturated cinnamic acid derivatives containing Evans type chiral auxiliaries
Leitis, Zigmārs,Lūsis, Viesturs
, p. 843 - 851 (2016/09/02)
Cinnamides containing oxazolidin-2-one type auxiliaries have been prepared. A novel pathway to chiral 4-aryl-6-methyl-3,4-dihydrocoumrines via the asymmetric conjugate addition of arylmagnesium bromides to these cinnamides is described.
Doubly diastereoselective conjugate addition of enantiopure lithium amides to enantiopure N-enoyl oxazolidin-2-ones: A mechanistic probe
Davies, Stephen G.,Fletcher, Ai M.,Hermann, Gesine J.,Poce, Giovanna,Roberts, Paul M.,Smith, Andrew D.,Sweet, Miles J.,Thomson, James E.
experimental part, p. 1635 - 1648 (2010/10/18)
The doubly diastereoselective conjugate addition of the antipodes of lithium N-benzyl-N-(α-methylbenzyl)amide to a range of enantiopure N-enoyl oxazolidin-2-ones has been used as a mechanistic probe to determine that the reactive conformation is the anti-s-cis form. The β-amino carbonyl products resulting from these conjugate addition reactions are useful templates for further elaboration into an α,β,α-pseudotripeptide.