A FACILE SYNTHESIS OF 2,3-DIHYDROXYKETONES FROM 1,2-DIKETONES AND ALDEHYDES USING SAMARIUM DIIODIDE

被引：7

作者：

MIYOSHI, N

TAKEUCHI, S

OHGO, Y

机构：

来源：

CHEMISTRY LETTERS | 1993年 / 06期

关键词：

D O I：

10.1246/cl.1993.959

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

In the presence of samarium diiodide, 1,2-diketones react with aldehydes to afford the corresponding 2,3-dihydroxyketones in good yields with moderate diastereoselectivity. The reaction of unsymmetrical 1,2-diketones with aldehydes gives the products with high regioselectivities.

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页码：959 / 962

页数：4

相关论文

共 10 条

[1] A FACILE SYNTHESIS OF ALPHA,BETA-DIHYDROXYKETONES VIA TIN(IV) ENEDIOLATES BY UTILIZING THE REDUCING POWER OF BIS(2-PYRIDINETHIOLATO)TIN(II) [J].

ICHIKAWA, J ;

MUKAIYAMA, T .

CHEMISTRY LETTERS, 1985, (07) :1009-1012

[2] A MILD AND CONVENIENT METHOD FOR THE REDUCTION OF ORGANIC HALIDES BY USING A SMI2-THF SOLUTION IN THE PRESENCE OF HEXAMETHYLPHOSPHORIC TRIAMIDE (HMPA) [J].

INANAGA, J ;

ISHIKAWA, M ;

YAMAGUCHI, M .

CHEMISTRY LETTERS, 1987, (07) :1485-1486

[3] TIN(II) ENEDIOLATE FROM METHYLGLYOXAL [J].

MUKAIYAMA, T ;

TSUZUKI, R ;

KATO, J .

CHEMISTRY LETTERS, 1983, (12) :1825-1828

[4] A STEREOSELECTIVE SYNTHESIS OF METHYL D-GLUCOSAMINATE VIA TIN(II) ENEDIOLATE FORMED FROM FURYLGLYOXAL [J].

MUKAIYAMA, T ;

TSUZUKI, R ;

KATO, J .

CHEMISTRY LETTERS, 1985, (06) :837-840

[5] A NOVEL METHOD FOR THE SYNTHESIS OF ALPHA,BETA-DIHYDROXY KETONES VIA TIN(II) ENEDIOLATES [J].

MUKAIYAMA, T ;

KATO, J ;

YAMAGUCHI, M .

CHEMISTRY LETTERS, 1982, (08) :1291-1294

[6] EFFICIENT FORMATION OF PINACOLS FROM ALDEHYDES OR KETONES MEDIATED BY SAMARIUM DIIODIDE [J].

NAMY, JL ;

SOUPPE, J ;

KAGAN, HB .

TETRAHEDRON LETTERS, 1983, 24 (08) :765-766

[7]

NAMY JL, 1977, CHEM REV, V1, P1

[8] A NEW SYNTHESIS OF ALPHA BETA-DIHYDROXY KETONES VIA OXYPHOSPHORANES . CONDENSATION OF ALIPHATIC ALPHA-DIKETONES WITH ALDEHYDES BY MEANS OF TRIALKYL PHOSPHITES . P31 AND H1 NUCLEAR MAGNETIC RESONANCE SPECTRA [J].

RAMIREZ, F ;

PATWARDH.AV ;

RAMANATH.N ;

DESAI, NB ;

GRECO, CV ;

HELLER, SR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (03) :543-&

[9] SMI2-(CHIRAL AUXILIARY)-INDUCED ASYMMETRIC REDUCTION [J].

TAKEUCHI, S ;

OHGO, Y .

CHEMISTRY LETTERS, 1988, (03) :403-404

[10] ASYMMETRIC-SYNTHESIS OF BENZOIN BY SMI2-MEDIATED ENANTIOSELECTIVE PROTONATION [J].

TAKEUCHI, S ;

MIYOSHI, N ;

HIRATA, K ;

HAYASHIDA, H ;

OHGO, Y .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1992, 65 (07) :2001-2003