A NONENZYMATIC, ASYMMETRIC-SYNTHESIS OF DICYCLOPENTADIENONE

被引：12

作者：

CHILDS, BJ ^{[1
]}

EDWARDS, GL ^{[1
]}

机构：

[1] UNIV NEW S WALES,SCH MED,POB 1,KENSINGTON,NSW 2033,AUSTRALIA

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 33期

关键词：

D O I：

10.1016/S0040-4039(00)73992-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A simple synthetic method for the preparation of optically active ''dicyclopentadienone'' is presented. The procedure involves the reaction of the magnesium enolate of the racemic ketone (2) with S(S)-menthyl-p-toluenesulfinate, giving a beta-ketosulfoxide as a single diastereoisomer. Conversions to enone (1) or saturated ketone (2) proceed with good optical and chemical yields.

引用

页码：5341 / 5342

页数：2

共 15 条

[1]

CARRENO MC, 1990, TETRAHEDRON LETT, V31, P6653

[2] SYNTHESIS OF CHIRAL CYCLIC ALPHA-PARA-TOLYLSULFINYL KETONES [J].

CARRENO, MC ;

RUANO, JLG ;

PEDREGAL, C ;

RUBIO, A .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (07) :1335-1337

[3] METHYLSULFINYL CARBANION (CH3-SO-CH2-) . FORMATION AND APPLICATIONS TO ORGANIC SYNTHESIS [J].

COREY, EJ ;

CHAYKOVSKY, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (06) :1345-+

[4] DIELS-ALDER REACTIONS OF CYCLOALKENONES .3. EFFECTS OF SPECIFIC REACTION PARAMETERS [J].

FRINGUELLI, F ;

PIZZO, F ;

TATICCHI, A ;

WENKERT, E .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (17) :2802-2808

[5] N,S-DIMETHYL-S-PHENYLSULFOXIMINE - A REAGENT FOR THE OPTICAL RESOLUTION OF KETONES [J].

JOHNSON, CR ;

ZELLER, JR .

TETRAHEDRON, 1984, 40 (08) :1225-1233

[6] A STEREOSPECIFIC FORMAL SYNTHESIS OF CLAVULONES FROM TRICYCLO[5.2.1.0(2,6)]DECADIENONE EPOXIDES [J].

KLUNDER, AJH ;

ZWANENBURG, B ;

LIU, ZY .

TETRAHEDRON LETTERS, 1991, 32 (26) :3131-3132

[7] LINEARLY FUSED VS BRIDGED REGIOSELECTION IN THE INTRAMOLECULAR 1,3-DIYL TRAPPING REACTION [J].

MASJEDIZADEH, MR ;

DANNECKERDOERIG, I ;

LITTLE, RD .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (09) :2742-2752

[8] PREPARATION OF (+)-N,S-DIMETHYL-S-PHENYLSULFOXIMINE AND (-)-N,S-DIMETHYL-S-PHENYLSULFOXIMINE VIA AN IMPROVED RESOLUTION - ACCURATE DETERMINATION OF VERY HIGH ENANTIOMERIC PURITIES BY ON-COLUMN GC ANALYSIS OF DIASTEREOMERIC DERIVATIVES [J].

SHINER, CS ;

BERKS, AH .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (23) :5542-5545

[9] A CONCISE STEREOCONTROLLED TOTAL SYNTHESIS OF (+)-ESTRONE [J].

TAKANO, S ;

MORIYA, M ;

OGASAWARA, K .

TETRAHEDRON LETTERS, 1992, 33 (14) :1909-1910

[10] EXPEDIENT PREPARATION AND ENANTIOMERIZATION OF OPTICALLY PURE DICYCLOPENTADIENONE (TRICYCLO[5.2.1.0(2,6)]DECA-4,8-DIEN-3-ONE) [J].

TAKANO, S ;

INOMATA, K ;

TAKAHASHI, M ;

OGASAWARA, K .

SYNLETT, 1991, (09) :636-638

← 1 2 →