Asymmetric tricarbonyliron complexation of cyclohexadiene directed by chiral ester and amide auxiliaries

被引：5
|
作者：
Ong, CW
Huang, CS
Chang, TH
机构：
[1] Department of Chemistry, National Sun Yat Sen University, Kaoshiung
来源：
ORGANOMETALLICS | 1996年 / 15卷 / 20期
关键词：
D O I：
10.1021/om960376e
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
Coupling of (+)-menthol, (+)-phenylethylamine and (-)-proline methyl ester with 4-methoxy-1-cyclohexa-2,4-dieneacetic acid gave the chiral ester 1 and amides 2 and 3, respectively, which were then isomerized into the 1,3-dienes. The diastereoselection induced by the chiral ester and amide auxiliaries during complexation with nonacarbonyliron was quite encouraging. The diastereomeric ratios of the ester- and amide-Fe(CO)(3) complexes formed were determined directly from the H-1 NMR integration of observable diastereotopic chemical shifts.
引用
收藏
页码：4334 / 4336
页数：3
相关论文
共 50 条
  • [31] THE USE OF CARBOHYDRATES AS CHIRAL AUXILIARIES IN HYDROXYL-DIRECTED REACTIONS
    CHARETTE, AB
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1993, 205 : 67 - CARB
  • [32] CHIRALITY CONTROL BY THE AID OF 2,2-DIMETHYLOXAZOLIDINE CHIRAL AUXILIARIES - HIGHLY 1,4-CHIRAL INDUCTIVE ASYMMETRIC ALKYLATIONS OF AMIDE ENOLATES
    KANEMASA, S
    UENO, K
    ONIMURA, K
    KIKUKAWA, T
    YAMAMOTO, H
    TETRAHEDRON, 1995, 51 (38) : 10453 - 10462
  • [33] AMINO-ACID ESTERS AS CHIRAL AUXILIARIES IN ASYMMETRIC CYCLOADDITIONS
    WALDMANN, H
    BRAUN, M
    GAZZETTA CHIMICA ITALIANA, 1991, 121 (06): : 277 - 284
  • [34] Asymmetric catalysis in the complexation of prochiral dienes by the tricarbonyliron fragment: A novel methodology for the enantioselective synthesis of planar chiral tricarbonyl(diene)iron complexes
    Knolker, HJ
    Hermann, H
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (03): : 341 - 344
  • [35] Asymmetric Induction via Metalation of Succinic Esters and Amide Using S(+) Menthol and R(+) 1-Phenylethylamine as Chiral Auxiliaries
    Auj e Sana
    Khan, Sher W.
    Ambreen, Nida
    Arfan, Muhammad
    Zaidi, Javid H.
    Khan, Khalid M.
    Perveen, Shahnaz
    Miana, Ghulam A.
    LETTERS IN ORGANIC CHEMISTRY, 2012, 9 (09) : 632 - 638
  • [36] New Isoxazolidine-based Chiral Auxiliaries for Asymmetric Syntheses
    Tetrahedron Lett, 18 (3261):
  • [37] New strategy for the use of chiral auxiliaries in asymmetric synthesis.
    Feuillet, FJ
    Bull, SD
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2003, 225 : U357 - U357
  • [38] Carbohydrates as chiral auxiliaries in asymmetric addition and cycloaddition reactions.
    Andersen, R
    DiCesare, JC
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1999, 217 : U368 - U368
  • [39] ASYMMETRIC INDUCTION USING BILE-ACIDS AS CHIRAL AUXILIARIES
    NAIR, V
    PRABHAKARAN, J
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1995, 34 (10): : 841 - 843
  • [40] CARBOHYDRATES AS CHIRAL AUXILIARIES - ASYMMETRIC CYCLOPROPANATION REACTION OF ACYCLIC OLEFINS
    CHARETTE, AB
    COTE, B
    MARCOUX, JF
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (21) : 8166 - 8167
12345