New, highly efficient syntheses of rac-, (R)- and (S)-4-hydroxy-2-cyclohexenone

被引：27

作者：

de March, P ^{[1
]}

Escoda, M ^{[1
]}

Figueredo, M ^{[1
]}

Font, J ^{[1
]}

García-García, E ^{[1
]}

Rodríguez, S ^{[1
]}

机构：

[1] Univ Autonoma Barcelona, Dept Quim, Bellaterra 08193, Spain

来源：

TETRAHEDRON-ASYMMETRY | 2000年 / 11卷 / 22期

关键词：

D O I：

10.1016/S0957-4166(00)00451-1

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Both enantiomers of 4-hydroxy-2-cyclohexenone have been synthesised from chiral p-benzoquinone equivalents through very short and simple sequences in good overall yields. (C) 2000 Published by Elsevier Science Ltd.

引用

页码：4473 / 4483

页数：11

共 23 条

[1] SYNTHESIS OF 2 USEFUL, ENANTIOMERICALLY PURE DERIVATIVES OF (S)-4-HYDROXY-2-CYCLOHEXENONE [J].

AUDIA, JE ;

BOISVERT, L ;

PATTEN, AD ;

VILLALOBOS, A ;

DANISHEFSKY, SJ .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (15) :3738-3740

[2] RUTHENIUM-CATALYZED ISOMERIZATION OF ALLYLIC ALCOHOLS TO SATURATED KETONES [J].

BACKVALL, JE ;

ANDREASSON, U .

TETRAHEDRON LETTERS, 1993, 34 (34) :5459-5462

[3] COTPP-CATALYZED REACTION OF SATURATED BICYCLIC ENDOPEROXIDES [J].

BALCI, M ;

AKBULUT, N .

TETRAHEDRON, 1985, 41 (07) :1315-1322

[4] CYCLOPENTADIENES AS CHIRAL TEMPLATES .4. AN EASY ACCESS TO (S)-HYDROXYCYCLOHEXENONE AND (R)-HYDROXYCYCLOHEXENONE [J].

BRUNJES, R ;

TILSTAM, U ;

WINTERFELDT, E .

CHEMISCHE BERICHTE, 1991, 124 (07) :1677-1678

[5] SHORT AND EFFICIENT SYNTHESIS OF (R)-4-HYDROXY-4-METHYL CYCLOHEXENONE [J].

BUENO, AB ;

CARRENO, MC ;

RUANO, JLG ;

FISCHER, J .

TETRAHEDRON LETTERS, 1995, 36 (21) :3737-3740

[6]

CARRENO MC, 1990, TETRAHEDRON LETT, V31, P6653

[7] ENANTIOSELECTIVE EPOXIDATION OF CYCLIC 1,3-DIENES CATALYZED BY A STERICALLY AND ELECTRONICALLY OPTIMIZED (SALEN)MN COMPLEX [J].

CHANG, S ;

HEID, RM ;

JACOBSEN, EN .

TETRAHEDRON LETTERS, 1994, 35 (05) :669-672

[8] TOTAL SYNTHESES OF ML-236A AND COMPACTIN BY COMBINING THE LACTONIC (SILYL) ENOLATE REARRANGEMENT AND ALDEHYDE-DIENE CYCLOCONDENSATION TECHNOLOGIES [J].

DANISHEFSKY, SJ ;

SIMONEAU, B .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (07) :2599-2604

[9] Diels-Alder reactions of masked p-benzoquinones [J].

de March, P ;

Figueredo, M ;

Font, J ;

Rodríguez, S .

TETRAHEDRON, 2000, 56 (22) :3603-3609

[10] EFFICIENT MASKING OF P-BENZOQUINONE IN NITRONE CYCLOADDITION CHEMISTRY [J].

DEMARCH, P ;

ESCODA, M ;

FIGUEREDO, M ;

FONT, J .

TETRAHEDRON LETTERS, 1995, 36 (47) :8665-8668

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