A practical synthesis of α-amino ketones via aryllithium addition to N-boc-α-amino acids

被引:0
|
作者
Florjancic, AS [1 ]
Sheppard, GS [1 ]
机构
[1] Abbott Labs, Global Pharmaceut Prod Res & Dev, Abbott Pk, IL 60064 USA
来源
SYNTHESIS-STUTTGART | 2003年 / 11期
关键词
arylations; amino acids; lithiation; ketones; nucleophilic additions;
D O I
暂无
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The reaction of N-Boc-alpha-amino acids with aryllithium reagents followed by removal of the nitrogen protecting group provides enantiomerically pure alpha-amino aryl ketones as their corresponding HCl salts. This practical two-step sequence gives rapid access to a pharmaceutically interesting class of compounds from commercially available starting materials.
引用
收藏
页码:1653 / 1656
页数:4
相关论文
共 50 条
  • [11] Synthesis of (S)-N-Boc-α-aminopirnelic and (S)-N-Boc-α-aminosuberic monoester and diester
    Wei, Miao
    Wei-Liang, Xu
    Zhi-Liu, Zhang
    Ru-Jian, Ma
    Shu-Hui, Chen
    Ge, Li
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2007, 27 (10) : 1264 - 1267
  • [12] Cyclization of N-Boc-(E)-α,β-unsaturated γ-amino acid active esters into N-Boc-(Z)-α,β-unsaturated γ-lactams through E → Z isomerization
    Singh, Manjeet
    Kumar, Manish
    Nalawade, Sachin A.
    Puneeth Kumar, DRGKoppalu R.
    Gopi, Hosahudya N.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2023, 21 (18) : 3766 - 3769
  • [13] A STEREOSELECTIVE SYNTHESIS OF N-BOC-ALPHA-AMINO ALCOHOLS AND ALPHA-AMINO-ACIDS
    ERMERT, P
    MEYER, J
    STUCKI, C
    SCHNEEBELI, J
    OBRECHT, JP
    TETRAHEDRON LETTERS, 1988, 29 (11) : 1265 - 1268
  • [14] Concise synthesis of valuable chiral N-Boc-β-benzyl-β-amino acid via construction of chiral N-Boc-3-benzyl-5-oxoisoxazolidine through cross-metathesis/conjugate addition/oxidation
    Hong-Tao Jiang
    Hao-Ling Gao
    Cheng-Sheng Ge
    Chinese Chemical Letters, 2017, 28 (02) : 471 - 475
  • [15] Synthesis of Boc-Amino Tetrazoles Derived from α-Amino Acids
    Sureshbabu, Vommina V.
    Naik, Shankar A.
    Nagendra, G.
    SYNTHETIC COMMUNICATIONS, 2009, 39 (03) : 395 - 406
  • [16] Concise synthesis of valuable chiral N-Boc-β-benzyl-β-amino acid via construction of chiral N-Boc-3-benzyl-5-oxoisoxazolidine through cross-metathesis/conjugate addition/oxidation
    Jiang, Hong-Tao
    Gao, Hao-Ling
    Ge, Cheng-Sheng
    CHINESE CHEMICAL LETTERS, 2017, 28 (02) : 471 - 475
  • [17] Synthesis of highly enantiomerically enriched N-Boc-alpha-amino ketones from pseudoephedrine N-Boc-alpha-amino acid amides.
    Myers, AG
    Yoon, T
    TETRAHEDRON LETTERS, 1995, 36 (52) : 9429 - 9432
  • [18] β-isocupreidine-catalyzed baylis -: Hillman reaction of chiral N-boc-α-amino aldehydes
    Nakano, Ayako
    Takahashi, Keisuke
    Ishihara, Jun
    Hatakeyama, Susumi
    ORGANIC LETTERS, 2006, 8 (23) : 5357 - 5360
  • [19] A CONCISE ENANTIOSELECTIVE SYNTHESIS OF ALLYLAMINES AND N-BOC-BETA-AMINO ACIDS
    ALCON, M
    CANAS, M
    POCH, M
    MOYANO, A
    PERICAS, MA
    RIERA, A
    TETRAHEDRON LETTERS, 1994, 35 (10) : 1589 - 1592
  • [20] SYNTHESIS OF N-(CARBOXYMETHYL)BENZYL ESTERS OF BOC-AMINO-ACIDS
    KULIKOV, SV
    SOKOLOVA, NY
    ZHURNAL OBSHCHEI KHIMII, 1992, 62 (10): : 2397 - 2398