Two methods for the preparation of 2-cyclohexenones from resin-bound 1,3-cyclohexanedione

被引：27

作者：

Fraley, ME

Rubino, RS

机构：

[1] Department of Medicinal Chemistry, Merck Research Laboratories, West Point

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 19期

关键词：

D O I：

10.1016/S0040-4039(97)00631-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The addition of organolithium or Grignard reagents to vinylogous ester resin 1 followed by mild hydrolysis of product resins 2 provides 3-alkyl-2-cyclohexenones in high purity (>95%). Alternatively, conversion of 1 to vinyl triflate resin 4 followed by palladium-mediated couplings with aryl boronic acids and hydrolysis furnishes 3-aryl-2-cyclohexenones in lower yield, but exceptional purity. (C) 1997 Elsevier Science Ltd.

引用

收藏

页码：3365 / 3368

页数：4

相关论文

共 10 条

[1] CARBON-CARBON BOND-FORMING METHODS ON SOLID SUPPORT - UTILIZATION OF KENNER SAFETY-CATCH LINKER [J].

BACKES, BJ ;

ELLMAN, JA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (24) :11171-11172

[2] BIARYL SYNTHESIS VIA SUZUKI COUPLING ON A SOLID SUPPORT [J].

FRENETTE, R ;

FRIESEN, RW .

TETRAHEDRON LETTERS, 1994, 35 (49) :9177-9180

[3] Organic chemistry on solid supports [J].

Fruchtel, JS ;

Jung, G .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (01) :17-42

[4] SOLID-PHASE SYNTHESIS OF HIGHLY SUBSTITUTED PEPTOID 1(2H)-ISOQUINOLINONES [J].

GOFF, DA ;

ZUCKERMANN, RN .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (18) :5748-5749

[5] Solid-phase Suzuki coupling for C-C bond formation [J].

Guiles, JW ;

Johnson, SG ;

Murray, WV .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (15) :5169-5171

[6] Solid-phase organic reactions: A review of the recent literature [J].

Hermkens, PHH ;

Ottenheijm, HCJ ;

Rees, D .

TETRAHEDRON, 1996, 52 (13) :4527-4554

[7] A METHOD FOR THE REGIOSPECIFIC SYNTHESIS OF ENOL TRIFLATES BY ENOLATE TRAPPING [J].

MCMURRY, JE ;

SCOTT, WJ .

TETRAHEDRON LETTERS, 1983, 24 (10) :979-982

[8] THE PALLADIUM-CATALYZED CROSS-COUPLING REACTION OF PHENYLBORONIC ACID WITH HALOARENES IN THE PRESENCE OF BASES [J].

MIYAURA, N ;

YANAGI, T ;

SUZUKI, A .

SYNTHETIC COMMUNICATIONS, 1981, 11 (07) :513-519

[9] Synthesis and applications of small molecule libraries [J].

Thompson, LA ;

Ellman, JA .

CHEMICAL REVIEWS, 1996, 96 (01) :555-600

[10] HECK REACTIONS IN SOLID-PHASE SYNTHESIS [J].

YU, KL ;

DESHPANDE, MS ;

VYAS, DM .

TETRAHEDRON LETTERS, 1994, 35 (48) :8919-8922