trans-cyclopropyl β-amino acid derivatives via asymmetric cyclopropanation using a (salen)Ru(II) catalyst

被引：47
作者：
Miller, JA
Hennessy, EJ
Marshall, WJ
Scialdone, MA
Nguyen, ST
机构：
[1] DuPont Co Inc, Cent Res & Dev, Expt Stn, Wilmington, DE 19880 USA
[2] Northwestern Univ, Dept Chem, Evanston, IL 60208 USA
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 68卷 / 20期
关键词：
D O I：
10.1021/jo0344079
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
trans-Cyclopropyl beta-amino acid derivatives can be synthesized in five steps with excellent enantioselectivities using a chiral (Salen)Ru(II) cyclopropanation catalyst in the key asymmetry-induction step. This facile synthesis proceeds with high overall yield and can be used to prepare a number of carbamate-protected (Cbz and Boc are demonstrated) beta-amino acid derivatives.
引用
收藏
页码：7884 / 7886
页数：3
相关论文
共 46 条
  • [11] SYNTHESIS OF CYCLOPROPYL CARBOCYCLIC NUCLEOSIDES
    CSUK, R
    VONSCHOLZ, Y
    [J]. TETRAHEDRON, 1994, 50 (35) : 10431 - 10442
  • [12] Davies HML, 2002, ANGEW CHEM INT EDIT, V41, P2197, DOI 10.1002/1521-3773(20020617)41:12<2197::AID-ANIE2197>3.0.CO
  • [13] 2-N
  • [14] DAVIES SG, 1993, SYNLETT, P461
  • [15] The twists and turns of β-peptides
    DeGrado, WF
    Schneider, JP
    Hamuro, Y
    [J]. JOURNAL OF PEPTIDE RESEARCH, 1999, 54 (03): : 206 - 217
  • [16] CHIRAL RHODIUM(II) CARBOXAMIDES - A NEW CLASS OF CATALYSTS FOR ENANTIOSELECTIVE CYCLOPROPANATION REACTIONS
    DOYLE, MP
    BRANDES, BD
    KAZALA, AP
    PIETERS, RJ
    JARSTFER, MB
    WATKINS, LM
    EAGLE, CT
    [J]. TETRAHEDRON LETTERS, 1990, 31 (46) : 6613 - 6616
  • [17] DUGGAN ME, 1989, SYNTHESIS-STUTTGART, P131
  • [18] A general method for the synthesis of enantiomerically pure β-substituted, β-amino acids through α-substituted succinic acid derivatives
    Evans, DA
    Wu, LD
    Wiener, JJM
    Johnson, JS
    Ripin, DHB
    Tedrow, JS
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (17) : 6411 - 6417
  • [19] FUKUDA T, 1995, SYNLETT, P825
  • [20] The chemistry of 2-aminocycloalkanecarboxylic acids
    Fülöp, F
    [J]. CHEMICAL REVIEWS, 2001, 101 (07) : 2181 - 2204
12345