AN EASY ACCESS TO VINYLBORONATES BETA-SUBSTITUTED BY A KETO GROUP

被引:23
作者
JEHANNO, E [1 ]
VAULTIER, M [1 ]
机构
[1] UNIV RENNES 1,CNRS,PHYSICOCHIM STRUCT GRP,F-35042 RENNES,FRANCE
关键词
D O I
10.1016/0040-4039(95)00812-Q
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An easy access to 3-borylacrolein 4 is described. This alpha,beta-insaturated aldehyde was smoothly reacted with organozinc or organocuprates to give the corresponding allyl alcohols 5 in good yields. The alpha,beta-unsaturated ketones 6 were easily obtained by oxidation of 5 with PCC. This overall sequence constitutes a general synthesis of these hitherto interesting new compounds.
引用
收藏
页码:4439 / 4442
页数:4
相关论文
共 11 条
[1]  
BROWN HC, 1980, SYNTHESIS-STUTTGART, P151
[2]  
BUNDY GL, 1978, TETRAHEDRON LETT, P41
[3]   A USEFUL 12-I-5 TRIACETOXYPERIODINANE (THE DESS-MARTIN PERIODINANE) FOR THE SELECTIVE OXIDATION OF PRIMARY OR SECONDARY ALCOHOLS AND A VARIETY OF RELATED 12-I-5 SPECIES [J].
DESS, DB ;
MARTIN, JC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (19) :7277-7287
[4]   PREPARATION AND REACTIVITY OF CHIRAL BETA-AMIDO-ALKYLZINC IODIDES AND RELATED CONFIGURATIONALLY STABLE ZINC ORGANOMETALLICS [J].
DUDDU, R ;
ECKHARDT, M ;
FURLONG, M ;
KNOESS, HP ;
BERGER, S ;
KNOCHEL, P .
TETRAHEDRON, 1994, 50 (08) :2415-2432
[5]  
GONDA J, 1993, SYNTHESIS-STUTTGART, P729
[6]  
HOFFMANN RW, 1991, LIEBIGS ANN CHEM, P1195
[7]   PREPARATION OF NEW CLASSES OF ALIPHATIC, ALLYLIC, AND BENZYLIC ZINC AND COPPER REAGENTS BY THE INSERTION OF ZINC DUST INTO ORGANIC HALIDES, PHOSPHATES, AND SULFONATES [J].
JUBERT, C ;
KNOCHEL, P .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (20) :5425-5431
[8]   PREPARATION AND REACTIONS OF POLYFUNCTIONAL ORGANOZINC REAGENTS IN ORGANIC-SYNTHESIS [J].
KNOCHEL, P ;
SINGER, RD .
CHEMICAL REVIEWS, 1993, 93 (06) :2117-2188
[9]   DIELS-ALDER CYCLOADDITION OF 3-BORYLPROPENOIC ACID-DERIVATIVES AND THEIR USE AS SYNTHETIC EQUIVALENTS OF E-BETA-HYDROXY ACRYLIC-ACID AND E-BETA-HYDROXY VINYLAMINE [J].
RASSET, C ;
VAULTIER, M .
TETRAHEDRON, 1994, 50 (11) :3397-3406
[10]  
RASSETDELOGE C, 1994, B SOC CHIM FR, V131, P919