ENANTIOMERICALLY PURE 6-SUBSTITUTED 2-OXO-CYCLOHEXANECARBOXYLATES BY CONJUGATE ADDITION OF CUPRATES TO ASYMMETRIC SHIELDED 2-OXO-CYCLOHEXENECARBOXYLATES

被引：14

作者：

URBAN, E ^{[1
]}

RIEHS, G ^{[1
]}

KNUHL, G ^{[1
]}

机构：

[1] UNIV HEIDELBERG,INST ORGAN CHEM,D-69120 HEIDELBERG,GERMANY

来源：

TETRAHEDRON | 1995年 / 51卷 / 41期

关键词：

D O I：

10.1016/0040-4020(95)00676-Y

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Asymmetric shielded 2-oxo-cyclohexenecarboxylates 6n and 6x were prepared by transesterification of 2-oxo-cyclohexanecarboxylate 2 with camphor derived concave alcohols In and Ix and by subsequent introduction of a double bond via phenylselenides. Diastereoselective conjugate addition of equimolar amounts of mixed cuprates at -78 degrees C and deprotection by methanolysis gave enantiomerically pure 6-substituted 2-oxo-cyclohexanecarboxylates 14-19 and ent-14-19, valuable as chiral building blocks in natural product synthesis.

引用

页码：11149 / 11164

页数：16

共 10 条

[1] TOTAL SYNTHESIS OF (+/-)-HEPTELIDIC ACID [J].

DANISHEFSKY, SJ ;

MANTLO, N .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (24) :8129-8133

[2] CHIRALITY AS A PROBE IN BETA-KETO ESTER TAUTOMERISM [J].

DECICCO, CP ;

BUCKLE, RN .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (03) :1005-1008

[3] ASYMMETRIC-SYNTHESIS OF BETA-SUBSTITUTED ALCANOIC ACIDS VIA HIGHLY STEREOSELECTIVE CONJUGATE ADDITIONS OF ORGANOCOPPER COMPOUNDS TO CHIRAL ENOATES [J].

HELMCHEN, G ;

WEGNER, G .

TETRAHEDRON LETTERS, 1985, 26 (49) :6051-6054

[4] A SIMPLE METHOD FOR THE EFFICIENT SYNTHESIS OF UNSATURATED BETA-DICARBONYL COMPOUNDS [J].

LIOTTA, D ;

BARNUM, C ;

PULEO, R ;

ZIMA, G ;

BAYER, C ;

KEZAR, HS .

JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (14) :2920-2923

[5] 2-THIENYL(CYANO)COPPER LITHIUM - A LOWER ORDER, STABLE CUPRATE IN A BOTTLE PRECURSOR TO HIGHER-ORDER REAGENTS [J].

LIPSHUTZ, BH ;

KOERNER, M ;

PARKER, DA .

TETRAHEDRON LETTERS, 1987, 28 (09) :945-948

[6] CAMPHORSULFONAMIDE-SHIELDED, ASYMMETRIC 1,4-ADDITIONS AND ENOLATE ALKYLATIONS - SYNTHESIS OF A SOUTHERN CORN-ROOTWORM PHEROMONE [J].

OPPOLZER, W ;

DUDFIELD, P ;

STEVENSON, T ;

GODEL, T .

HELVETICA CHIMICA ACTA, 1985, 68 (01) :212-215

[7] ASYMMETRIC CONJUGATE ADDITION [J].

ROSSITER, BE ;

SWINGLE, NM .

CHEMICAL REVIEWS, 1992, 92 (05) :771-806

[8] N,N-DIMETHYL-4-PYRIDINAMINE, A VERY EFFECTIVE ACYLATION CATALYST [J].

STEGLICH, W ;

HOFLE, G .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1969, 8 (12) :981-&

[9] PREPARATION OF BETA-KETO-ESTERS BY 4-DMAP-CATALYZED ESTER EXCHANGE [J].

TABER, DF ;

AMEDIO, JC ;

PATEL, YK .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (19) :3618-3619

[10]

URBAN E, 1994, SCI PHARM, V62, P195

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