Asymmetric synthesis of syn- and anti-alpha-deuterio-beta(3)-phenylalanine derivatives

作者：Davies Stephen G^*; Foster Emma M; McIntosh Catherine R; Roberts Paul M; Rosser Timothy E; Smith Andrew D; Thomson James E

来源：Tetrahedron: Asymmetry , 2011, 22(10): 1035-1050.

DOI：10.1016/j.tetasy.2011.06.008

The conjugate addition of lithium (S)-N-benzyl-N-(alpha-methylbenzyl)amide to a range of aryl substituted tert-butyl cinnamate esters followed by reaction of the resultant lithium beta-amino enolates with D2O provides access to anti configured alpha-deuterio-beta-aminocinnamate esters in high dr. The corresponding syn configured diastereoisomers were also obtained with high diastereoselectivity via the conjugate addition of lithium (5)-N-benzyl-N-(alpha-methylbenzyl)amide to a range of tert-butyl alpha-deuteriocinnamate esters followed by reaction of the resultant lithium beta-amino enolates with 2-pyridone. After deprotection both the syn- and anti-diastereoisomers of the corresponding alpha-deuterio-beta(3)-amino acids can be isolated in high dr.

• 出版日期2011-5-31