NOREPHEDRINE DERIVED 2-METHOXY OXAZOLIDINES AS CHIRAL FORMYL CATION EQUIVALENTS

被引:40
作者
BERNARDI, A
CARDANI, S
CARUGO, O
COLOMBO, L
SCOLASTICO, C
VILLA, R
机构
[1] DIPARTIMENTO CHIM ORGAN & IND, VIA VENEZIAN 21, I-20133 MILAN, ITALY
[2] UNIV SASSARI, DEPARTIMENTO CHIM, I-07100 SASSARI, ITALY
[3] UNIV PAVIA, DIPARTIMENTO CHIM INORGAN, I-27100 PAVIA, ITALY
关键词
D O I
10.1016/S0040-4039(00)94697-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Lewis acid catalyzed reaction of silylenolethers with 1 followed by a straightforward nondestructive removal of the chiral auxiliary affords the corresponding aldehydes in good e.e. Compound 1 represents the first effective chiral synthetic equivalent of formyl cation. © 1990.
引用
收藏
页码:2779 / 2782
页数:4
相关论文
共 16 条
  • [1] BASILE T, 1989, 5TH OMCOS V IUPAC C
  • [2] NOREPHEDRINE-DERIVED 2-ALKENYLOXAZOLIDINES - STEREOCHEMISTRY OF CYCLIZATION AND ALLYLIC STEREOCENTER DIRECTED ASYMMETRIC CONJUGATE ADDITION
    BERNARDI, A
    CARDANI, S
    PILATI, T
    POLI, G
    SCOLASTICO, C
    VILLA, R
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (08) : 1600 - 1607
  • [3] BIGALKE J, 1988, THESIS MARBURG
  • [4] A NOVEL SYNTHESIS OF HALF-PROTECTED 1,3-DICARBONYL COMPOUNDS
    HATANAKA, K
    TANIMOTO, S
    SUGIMOTO, T
    OKANO, M
    [J]. TETRAHEDRON LETTERS, 1981, 22 (34) : 3243 - 3244
  • [5] KUNISCH F, 1985, TETRAHEDRON LETT, P5433
  • [6] A PROCEDURE FOR DIETHOXYMETHYLATION OF KETONES
    MOCK, WL
    TSOU, HR
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (12) : 2557 - 2561
  • [7] HIGHLY ENANTIOSELECTIVE CLAISEN-TYPE ACYLATION AND DIECKMANN ANNULATION
    NAGAO, Y
    HAGIWARA, Y
    TOHJO, T
    HASEGAWA, Y
    OCHIAI, M
    SHIRO, M
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (25) : 5983 - 5986
  • [8] ALDOL CONDENSATIONS OF CHIRAL ETHYLKETONES - CONTROL BY CHIRAL BORON REAGENTS
    PATERSON, I
    LISTER, MA
    [J]. TETRAHEDRON LETTERS, 1988, 29 (05) : 585 - 588
  • [9] PATERSON I, 1981, TETRAHEDRON LETT, P2829
  • [10] ORTHO ESTERS AND DIALKOXYCARBENIUM IONS - REACTIVITY, STABILITY, STRUCTURE, AND NEW SYNTHETIC APPLICATIONS
    PINDUR, U
    MULLER, J
    FLO, C
    WITZEL, H
    [J]. CHEMICAL SOCIETY REVIEWS, 1987, 16 (01) : 75 - 87