ENANTIOSELECTIVE SYNTHESIS OF (S)-6-(2,3-DIHYDROXYPROPYL)-1,3-DIOXIN-4-ONES AND (R)-6-(2,3-DIHYDROXYPROPYL)-1,3-DIOXIN-4-ONES - THE VERSATILE BUILDING-BLOCKS OF 4-CARBON AND 6-CARBON BACKBONES

被引：8

作者：

SAKAKI, J

SUGITA, Y

SATO, M

KANEKO, C

机构：

来源：

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS | 1991年 / 06期

关键词：

D O I：

10.1039/c39910000434

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The Sharpless asymmetric epoxidation of 2,2-dimethyl-6-(3-hydroxy-1-propenyl)-1,3-dioxin-4-one using titanium tetraisopropoxide-diisopropyl tartrate followed by catalytic hydrogenation affords the title compounds as enantiomerically pure compounds, which act as versatile four- and six-carbon building blocks.

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页码：434 / 435

页数：2

相关论文

共 21 条

[1] SYNTHESIS AND BIOLOGICAL-ACTIVITY OF NEW HMG-COA REDUCTASE INHIBITORS .1. LACTONES OF PYRIDINE-SUBSTITUTED AND PYRIMIDINE-SUBSTITUTED 3,5-DIHYDROXY-6-HEPTENOIC (-HEPTANOIC) ACIDS [J].

BECK, G ;

KESSELER, K ;

BAADER, E ;

BARTMANN, W ;

BERGMANN, A ;

GRANZER, E ;

JENDRALLA, H ;

VONKEREKJARTO, B ;

KRAUSE, R ;

PAULUS, E ;

SCHUBERT, W ;

WESS, G .

JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (01) :52-60

[2]

DEMUTH M, 1989, SYNTHESIS-STUTTGART, P145

[3] CATALYTIC ASYMMETRIC EPOXIDATION AND KINETIC RESOLUTION - MODIFIED PROCEDURES INCLUDING INSITU DERIVATIZATION [J].

GAO, Y ;

HANSON, RM ;

KLUNDER, JM ;

KO, SY ;

MASAMUNE, H ;

SHARPLESS, KB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (19) :5765-5780

[4] PROCEDURE FOR THE CATALYTIC ASYMMETRIC EPOXIDATION OF ALLYLIC ALCOHOLS IN THE PRESENCE OF MOLECULAR-SIEVES [J].

HANSON, RM ;

SHARPLESS, KB .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (10) :1922-1925

[5] 1,3-DIOXIN-4-ONES AS VERSATILE INTERMEDIATES FOR ORGANIC-SYNTHESIS [J].

KANEKO, C ;

SATO, M ;

SAKAKI, JI ;

ABE, Y .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1990, 27 (01) :25-30

[6] THE 1ST PRACTICAL METHOD FOR ASYMMETRIC EPOXIDATION [J].

KATSUKI, T ;

SHARPLESS, KB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (18) :5974-5976

[7] A NITRILE OXIDE BASED ENTRY TO 2,3-DIHYDROPYRAN-4-ONES - SYNTHESIS OF A PROTECTED VERSION OF COMPACTIN LACTONE IN RACEMIC AND OPTICALLY-ACTIVE FORMS [J].

KOZIKOWSKI, AP ;

LI, CS .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (06) :778-785

[8]

MORI K, 1979, TETRAHEDRON, V35, P436

[9]

NOYORI R, 1989, MODERN SYNTHETIC MET, V5, P145

[10] SYNTHESIS OF 8-MEMBERED RING LACTONES FROM DIOXOLENONES [J].

PETASIS, NA ;

PATANE, MA .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (11) :836-837