DIASTEREOSELECTIVE OXIDATIVE COUPLING OF ENOLATES OF CHIRAL CARBOXYLIC-ACID DERIVATIVES

被引：49

作者：

LANGER, T ^{[1
]}

ILLICH, M ^{[1
]}

HELMCHEN, G ^{[1
]}

机构：

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

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 25期

关键词：

D O I：

10.1016/0040-4039(95)00786-C

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Enolates of chiral propionic acid amides were oxidatively dimerized with cupric salts or iodine with high simple as well as induced diastereoselectivity of up to 99:1. Intramolecular coupling of chiral dienolates of 1,7-heptanediamides led to a 1,2-disubstituted cyclopentane and a derivative of 1,2,6,7-cyclodecane tetracarboxylic acid.

引用

页码：4409 / 4412

页数：4

共 19 条

[1] PREPARATION OF SMALL RING CARBOCYCLES VIA INTRAMOLECULAR OXIDATIVE COUPLING OF BISENOLATES DERIVED FROM ALPHA,OMEGA-DIESTERS [J].

BABLER, JH ;

SARUSSI, SJ .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (15) :3462-3464

[2] TOTAL SYNTHESIS OF (+/-)-WIKSTROMOL [J].

BELLETIRE, JL ;

FRY, DF .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (20) :4724-4729

[3] OXIDATIVE COUPLING .2. THE TOTAL SYNTHESIS OF ENTEROLACTONE [J].

BELLETIRE, JL ;

FREMONT, SL .

TETRAHEDRON LETTERS, 1986, 27 (02) :127-130

[4] OXIDATIVE COUPLING OF CARBOXYLIC-ACID DIANIONS [J].

BELLETIRE, JL ;

SPLETZER, EG ;

PINHAS, AR .

TETRAHEDRON LETTERS, 1984, 25 (52) :5969-5972

[5] OXIDATIVE COUPLING OF CARBOXYLIC-ACID DIANIONS - THE TOTAL SYNTHESIS OF (+/-)-HINOKININ AND (+/-)-FOMENTARIC ACID [J].

BELLETIRE, JL ;

FRY, DF .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (12) :2549-2555

[6] DIASTEREOSELECTIVE ALKYLATION OF 3-ACYLIMIDAZOLIDIN-2-ONES - SYNTHESIS OF (R)-LAVANDULOL AND (S)-LAVANDULOL [J].

CARDILLO, G ;

DAMICO, A ;

ORENA, M ;

SANDRI, S .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (10) :2354-2356

[7]

DERRA R, 1986, THESIS U WURZBURG

[8]

ELIEL EL, 1994, STEREOCHEMISTRY ORGA, P77

[9]

FOX MA, 1988, J ORG CHEM, V53, P3745

[10]

HELMCHEN G, 1993, 6TH M STER PRAH, P29

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