Tandem oxidative radical decarboxylation-β-iodination of amino acids.: Application to the synthesis of chiral 2,3-disubstituted pyrrolidines

被引:30
作者
Boto, A [1 ]
Hernández, R [1 ]
Suárez, E [1 ]
机构
[1] CSIC, Inst Prod Nat & Agrobiol, Tenerife 38206, Spain
关键词
amino acids; radical decarboxylation; halogenation; nitrogen heterocycles; metathesis;
D O I
10.1016/S0040-4039(00)00188-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A mild and efficient procedure for the tandem decarboxylation-halogenation of alpha-amino acids is reported. The iodine is introduced at previously unfunctionalized positions, in good yields. The methodology has been used for the diastereoselective synthesis of 2,3-disubstituted pyrrolidines. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:2495 / 2498
页数:4
相关论文
共 9 条
  • [1] Asymmetric Synthesis of δ-Chloro-β-amino-N-sulfinyl Imidates as Versatile Chiral Building Blocks for the Synthesis of 2,3-Disubstituted Piperidines
    Semina, Elena
    Colpaert, Filip
    Van Hecke, Kristof
    De Kimpe, Norbert
    Mangelinckx, Sven
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (22) : 4847 - 4859
  • [2] Tandem Oxidative Cyclocondensation towards 2,3-Disubstituted Quinazolinones in the Presence of [Bmim][BF4] and Iodine
    Sofi, Firdoos Ahmad
    Sharma, Rohit
    Chakraborti, Asit K.
    Bharatam, Prasad, V
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 2019 (34) : 5887 - 5893
  • [3] Convenient and stereospecific synthesis of trans-1,3-disubstituted imidazolidines and their transformation to 2,3-diamino-3-phenylpropanoic acids
    Kavrakova, IK
    Lyapova, MJ
    COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 2000, 65 (10) : 1580 - 1586
  • [4] Free radical-mediated tandem reaction of dehydroamino acid derivative with π-allyl palladium complex:: Synthesis of α,α-disubstituted amino acids
    Miyabe, H
    Asada, R
    Yoshida, K
    Takemoto, Y
    SYNLETT, 2004, (03) : 540 - 542
  • [5] CuO Nanoparticle Catalyzed Synthesis of 2,3-Disubstituted Quinazolinones via Sequential N-Arylation and Oxidative C-H Amidation
    Modi, Anju
    Ali, Wajid
    Mohanta, Prakash R.
    Khatun, Nilufa
    Patel, Bhisma K.
    ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2015, 3 (10): : 2582 - 2590
  • [6] An Approach to the Synthesis of anti-β2,3-Amino Acids: Application of β-Trifluoroacetamidoorganozinc Reagents
    Bartrum, Hannah E.
    Jackson, Richard F. W.
    SYNLETT, 2009, (14) : 2257 - 2260
  • [7] Diastereo- and enantioselective synthesis of 2-substituted 1-aminocyclopropane-1-carboxylic acids. Application to the synthesis of protected 2,3-methiano analogs of ornithine and glutamic acid
    Frick, JA
    Klassen, JB
    Rapoport, H
    SYNTHESIS-STUTTGART, 2005, (11): : 1751 - 1756
  • [8] Design and synthesis of some new C2-symmetric chiral disulfonamides from amino acids and the application in diethylzinc addition to benzaldehyde
    Wang, JQ
    Zhong, M
    Lin, GQ
    CHINESE JOURNAL OF CHEMISTRY, 1998, 16 (01) : 65 - 77
  • [9] Lewis acid activation of chiral 2-trifluoromethyl-1,3-oxazolidines.: Application to the stereoselective synthesis of trifluoromethylated amines, α- and β-amino acids
    Lebouvier, N
    Laroche, C
    Huguenot, F
    Brigaud, T
    TETRAHEDRON LETTERS, 2002, 43 (15) : 2827 - 2830