📜(3R,5R,6S)-4-(Benzyloxycarbonyl)-5,6-Diphenyl-3-(Phenylmethyl)-2,3,5,6-Tetrahydro-4H-1,4-Oxazin-2-One置于palladium Dichloride 盐酸,氢气体系中,用 四氢呋喃,乙醇 作为反应溶剂,化学反应 22.0H,反应生成 D-苯丙氨酸乙酯盐酸盐
参考文献:Asymmetric Synthesis Of Monosubstituted And .Alpha.,.Alpha.-Disubstituted .Alpha.-Amino Acids Via Diastereoselective Glycine Enolate Alkylations
标题:Asymmetric Synthesis Of Monosubstituted And .Alpha.,.Alpha.-Disubstituted .Alpha.-Amino Acids Via Diastereoselective Glycine Enolate Alkylations
摘要:The Enolates Derived From The Optically Active (5S,6R)-And (5R,6S)-4(Tert-Butyloxycarbonyl)-5,6-Diphenyl-2,3,5,6-Tetrahydro-4H-1,4-Oxazin-2-One (1A,B) And (5S,6R)-And (5R,6S)-4-(Benzyloxycarbonyl)-5,6-Diphenyl-2,3,5,6-Tetrahydro-4H-1,4-Oxazin-2-Ones (2A,B) Efficiently Couple With Alkyl Halides To Afford The Corresponding Anti-Alpha-Monosubstituted Oxazinones (3 And 4). The Enolate Alkylation Of The Alpha-Monosubstituted Oxazinones (3 And 4) Provides The Corresponding Alpha,Alpha-Disubstituted Oxazinones (7 And 8). Dissolving-Metal Reduction Of The Homologated Oxazinones Allows The Direct Preparation Of T-Boc-Protected Alpha-Amino Acids. In The Case Of A Dissolving-Metal-Reducible Functionality,Hydrogenation Over A Pd0 Catalyst Furnishes The Zwitterionic Amino Acids. By Employing This Protocol Several Amino Acids Or Their Corresponding N-T-Boc Derivatives,Such As Allylglycine,Alanine,Phenylalanine,Beta-Ethylaspartic Acid,Alpha-Methylphenylalanine,N-(Tert-Butyloxycarbonyl)Dimethallylglycine,N-(Tert-Butyloxycarbonyl)-2-(2'-Propenyl)Norvaline,N-(Tert-Butyloxycarbonyl)-2-(3'-Methyl-2'-Butenyl)Alanine,N-(Tert-Butyloxycarbonyl)-2-(2'-Propenyl)Alanine,2-(3'-Phenylpropyl)Alanine,2-Amino-6-(Acetyloxy)Hexanoic Acid,And 2(Tert-Butyloxycarbonyl)Amino-6-[(P-Methoxybenzyl)Thio]Hexanoic Acid,Are Prepared In High Enantiomeric Excess.
DOI:10.1021/ja00024A038