Application of a Ritter-type reaction to the synthesis of chiral indane-derived C-2-symmetric bis(oxazolines)

被引:68
作者
Davies, IW
Senanayake, CH
Larsen, RD
Verhoeven, TR
Reider, PJ
机构
[1] Department of Process Research, Merck Research Laboratories, Rahway, NJ 07065
关键词
D O I
10.1016/0040-4039(95)02328-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Bis(oxazolines) 4, 6, 8, 9, 10, and 11 are prepared in a highly regio- and diastereo-selective manner from dinitriles and indanediol 3 in a Ritter-type reaction initiated by trifluoromethanesulfonic acid.
引用
收藏
页码:813 / 814
页数:2
相关论文
共 14 条
  • [1] SYNTHESIS OF OPTICALLY-ACTIVE BIS(2-OXAZOLINES) - CRYSTAL-STRUCTURE OF A 1,2-BIS(2-OXAZOLINYL)BENZENE.ZNCL2 COMPLEX
    BOLM, C
    WEICKHARDT, K
    ZEHNDER, M
    RANFF, T
    [J]. CHEMISCHE BERICHTE, 1991, 124 (05) : 1173 - 1180
  • [2] BIS(4,5-DIHYDROOXAZOLYL) DERIVATIVES IN ASYMMETRIC CATALYSIS
    BOLM, C
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1991, 30 (05): : 542 - 543
  • [3] HIGHLY DIASTEREOSELECTIVE DIELS-ALDER REACTION MEDIATED BY A CHIRAL AUXILIARY DERIVED FROM AMINO INDANOL - THE ROLE OF CONFORMATION ON DIASTEREOSELECTIVITY
    DAVIES, IW
    SENANAYAKE, CH
    CASTONGUAY, L
    LARSEN, RD
    VERHOEVEN, TR
    REIDER, PJ
    [J]. TETRAHEDRON LETTERS, 1995, 36 (42) : 7619 - 7622
  • [4] PREPARATION OF CHIRAL BISOXAZOLINES - OBSERVATIONS ON THE EFFECT OF SUBSTITUENTS
    DENMARK, SE
    NAKAJIMA, N
    NICAISE, OJC
    FAUCHER, AM
    EDWARDS, JP
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (15) : 4884 - 4892
  • [5] BIS(OXAZOLINES) AS CHIRAL LIGANDS IN METAL-CATALYZED ASYMMETRIC REACTIONS - CATALYTIC, ASYMMETRIC CYCLOPROPANATION OF OLEFINS
    EVANS, DA
    WOERPEL, KA
    HINMAN, MM
    FAUL, MM
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (02) : 726 - 728
  • [6] C-2-SYMMETRIC CATIONIC COPPER(II) COMPLEXES AS CHIRAL LEWIS-ACIDS - COUNTERION EFFECTS IN THE ENANTIOSELECTIVE DIELS-ALDER REACTION
    EVANS, DA
    MURRY, JA
    VONMATT, P
    NORCROSS, RD
    MILLER, SJ
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (07): : 798 - 800
  • [7] BIS(OXAZOLINE) COPPER-COMPLEXES AS CHIRAL CATALYSTS FOR THE ENANTIOSELECTIVE AZIRIDINATION OF OLEFINS
    EVANS, DA
    FAUL, MM
    BILODEAU, MT
    ANDERSON, BA
    BARNES, DM
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (12) : 5328 - 5329
  • [8] GHOSH AK, 1995, TETRAHEDRON LETT, V36, P6811, DOI 10.1016/0040-4039(95)01385-U
  • [9] ASYMMETRIC CATALYTIC CYCLOPROPANATION OF OLEFINS - BIS-OXAZOLINE COPPER-COMPLEXES
    LOWENTHAL, RE
    ABIKO, A
    MASAMUNE, S
    [J]. TETRAHEDRON LETTERS, 1990, 31 (42) : 6005 - 6008
  • [10] DIASTEREOSELECTIVE SYN-EPOXIDATION OF 2-ALKYL-4-ENAMIDES TO EPOXYAMIDES - SYNTHESIS OF THE MERCK HIV-1 PROTEASE INHIBITOR EPOXIDE INTERMEDIATE
    MALIGRES, PE
    UPADHYAY, V
    ROSSEN, K
    CIANCIOSI, SJ
    PURICK, RM
    ENG, KK
    REAMER, RA
    ASKIN, D
    VOLANTE, RP
    REIDER, PJ
    [J]. TETRAHEDRON LETTERS, 1995, 36 (13) : 2195 - 2198