CONJUGATE ADDITION TO 3-(PARA-TOLYLSULPHINYL)CHROMONE - A ROUTE TO 2-SUBSTITUTED CHROMONES AND CHIRAL 2-SUBSTITUTED CHROMAN-4-ONES

被引：34

作者：

SAENGCHANTARA, ST ^{[1
]}

WALLACE, TW ^{[1
]}

机构：

[1] UNIV SALFORD,DEPT CHEM & APPL CHEM,SALFORD M5 4WT,LANCS,ENGLAND

来源：

TETRAHEDRON | 1990年 / 46卷 / 18期

关键词：

D O I：

10.1016/S0040-4020(01)96020-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

3-(p-Tolylsulphinyl)chromone 3a undergoes diastereoselective conjugate addition of lithium dimethylcuprate, producing a mixture of 2-methyl-3-(p-tolylsulphinyl)chroman-4-ones. Heating the mixture to 140°C gives 2-methylchromone in quantitative yield. Desulphurisation of the mixed products from (S)-3a gives (S)-2-methylchroman-4-one with 90% e.e. Chelation of the carbonyl and sulphoxide oxygens during methyl addition accounts for the diastereoselection. © 1990.

引用

页码：6553 / 6564

页数：12

共 31 条

[1] STUDIES OF CHROMENS .2. SYNTHESIS OF 7-METHOXY-2,2-DIMETHYLCHROMEN-3-CARBOXYLIC ACID [J].

ANASTASIS, P ;

BROWN, PE .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1983, (01) :197-200

[2]

ARAKAWA H, 1960, LIEBIGS ANN CHEM, V636, P111

[3] STUDIES RELATED TO CHEMISTRY OF MELANINS .9. SYNTHESES OF SPECIFICALLY DEUTERIATED 3,4-DIHYDROXYPHENETHYLAMINES AND (+/)-3,4-DI-HYDROXYPHENYLALANINES [J].

BINNS, F ;

KING, JAG ;

PERCIVAL, A ;

ROBSON, NC ;

SWAN, GA .

JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1970, (08) :1134-&

[4]

CERNIANI A, 1959, GAZZ CHIM ITAL, V83, P843

[5] NEW SYNTHESIS OF KETONES [J].

COREY, EJ ;

CHAYKOVSKY, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1964, 86 (08) :1639-&

[6]

COREY EJ, 1979, TETRAHEDRON LETT, P399

[7] CYCLOADDITIONS OF SUBSTITUTED BENZOPYRAN-4-ONES TO ELECTRON-RICH DIENES - A NEW ROUTE TO XANTHONE DERIVATIVES [J].

CREMINS, PJ ;

SAENGCHANTARA, ST ;

WALLACE, TW .

TETRAHEDRON, 1987, 43 (13) :3075-3082

[8] ON THE SELECTIVITY OF DEPROTECTION OF BENZYL, MPM (4-METHOXYBENZYL) AND DMPM (3,4-DIMETHOXYBENZYL) PROTECTING GROUPS FOR HYDROXY FUNCTIONS [J].

HORITA, K ;

YOSHIOKA, T ;

TANAKA, T ;

OIKAWA, Y ;

YONEMITSU, O .

TETRAHEDRON, 1986, 42 (11) :3021-3028

[9] SYNTHESIS AND REACTIONS OF 4-CHROMANONES [J].

KABBE, HJ ;

WIDDIG, A .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1982, 21 (04) :247-256

[10]

KASHIWADA Y, 1984, CHEM PHARM BULL, V32, P3493

← 1 2 3 4 →