LEWIS ACID - MEDIATED ADDITION OF LITHIATED ALKYL PHENYL SULFONES AND OXIRANES - A METHOD FOR SYNTHESIS OF ALPHA,BETA-UNSATURATED KETONES

被引：12

作者：

MARCZAK, S ^{[1
]}

WICHA, J ^{[1
]}

机构：

[1] POLISH ACAD SCI,INST ORGAN CHEM,KASPRZAKA 44,PL-01224 WARSAW,POLAND

来源：

SYNTHETIC COMMUNICATIONS | 1990年 / 20卷 / 10期

关键词：

D O I：

10.1080/00397919008052868

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Efficiency of the reaction of lithiated alkyl aryl sulphones -(1-4) with oxiranes (5, 6) is increased by the presence of BF3 or CeCl3. The respective adducts (7. -14) were transformed into α,β-unsaturated ketones (15 - 22) with high yields. © 1990, Taylor & Francis Group, LLC. All rights reserved.

引用

页码：1511 / 1520

页数：10

共 36 条

[21]

JULIA M, 1976, B SOC CHIM FR II-CH, P513

[22]

KOCH P, 1983, B SOC CHIM FR, P1

[23]

KONDO K, 1975, TETRAHEDRON LETT, P2275

[24] TOTAL SYNTHESIS OF 15-OXO-13,14-DIHYDRO-PROSTAGLANDIN F2-ALPHA, A MAJOR METABOLITE OF PROSTAGLANDIN F2-ALPHA [J].

MARCZAK, S ;

WICHA, J .

SYNTHETIC COMMUNICATIONS, 1989, 19 (3-4) :633-639

[25] COUPLING OF ALLYLIC ALCOHOL EPOXIDES WITH SULFUR-STABILIZED ALLYLIC ANIONS [J].

MARSHALL, JA ;

ANDREWS, RC .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (10) :1602-1606

[26] SYNTHETIC STUDIES ON (+)-APLASMOMYCIN .2. STEREOSELECTIVE SYNTHESIS OF COREY KEY INTERMEDIATE, A FORMAL TOTAL SYNTHESIS [J].

NAKATA, T ;

SAITO, K ;

OISHI, T .

TETRAHEDRON LETTERS, 1986, 27 (52) :6345-6348

[27]

NORMANT H, 1964, CR HEBD ACAD SCI, V259, P1635

[28] TOTAL SYNTHESIS OF DEBROMOAPLYSIATOXIN AND APLYSIATOXIN [J].

PARK, P ;

BROKA, CA ;

JOHNSON, BF ;

KISHI, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (20) :6205-6207

[29]

SCHREKENBECK J, 1978, TETRAHEDRON, V1, P829

[30]

TAKAYAMA H, 1980, TETRAHEDRON LETT, V21, P5026

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