AN IMPROVED SYNTHESIS AND RESOLUTION OF (+/-)-CIS,CIS-SPIRO[4.4]NONANE-1,6-DIOL

被引：50

作者：

NIEMAN, JA ^{[1
]}

PARVEZ, M ^{[1
]}

KEAY, BA ^{[1
]}

机构：

[1] UNIV CALGARY,DEPT CHEM,CALGARY T2N 1N4,ALBERTA,CANADA

来源：

TETRAHEDRON-ASYMMETRY | 1993年 / 4卷 / 09期

关键词：

D O I：

10.1016/S0957-4166(00)82242-9

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

(+/-)-cis,cis-Spiro[4.4]nonane-1,6-diol (2) is synthesized stereoselectively in four steps (51%) beginning with ethyl 2-oxocyclopentanecarboxylate. An improved resolution of diol 2 is described by preparing diastereomeric ketals of (1R)-(+)-camphor. The relative stereochemistry of cis,cis-diol 2 is unambiguously assigned via an X-ray crystal structure of the bis-(p-nitrobenzoate) derivative.

引用

收藏

页码：1973 / 1976

页数：4

相关论文

共 32 条

[1] A new synthesis of 4-ketohexahydroindan [J].

Bachmann, WE ;

Struve, WS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1941, 63 :2589-2591

[2] THE CHIRAL POOL AS A SOURCE OF ENANTIOSELECTIVE CATALYSTS AND AUXILIARIES [J].

BLASER, HU .

CHEMICAL REVIEWS, 1992, 92 (05) :935-952

[3] BICYCLO[4.2.1]NON-1-EN-8-ONE - NOVEL ANTI-BREDT ENONE - SYNTHESIS OF NON-ENOLISABLE BETA-DIKETONES FROM OXO-ACIDS [J].

CARRUTHERS, W ;

ORRIDGE, A .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1977, (21) :2411-2416

[4] CHIRAL ORGANOSILICON COMPOUNDS IN ASYMMETRIC-SYNTHESIS [J].

CHAN, TH ;

WANG, D .

CHEMICAL REVIEWS, 1992, 92 (05) :995-1006

[5] SYNTHESIS AND PROPERTIES OF DERIVATIVES OF SPIRO [4.4]NONANE [J].

CRAM, DJ ;

STEINBERG, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1954, 76 (10) :2753-2757

[6] ASYMMETRIC HYDROXYLATION OF ENOLATES WITH N-SULFONYLOXAZIRIDINES [J].

DAVIS, FA ;

CHEN, BC .

CHEMICAL REVIEWS, 1992, 92 (05) :919-934

[7] CHIRAL TITANIUM COMPLEXES FOR ENANTIOSELECTIVE ADDITION OF NUCLEOPHILES TO CARBONYL GROUPS [J].

DUTHALER, RO ;

HAFNER, A .

CHEMICAL REVIEWS, 1992, 92 (05) :807-832

[8] ASYMMETRIC C-C-BOND FORMATION WITH TITANIUM CARBOHYDRATE COMPLEXES [J].

DUTHALER, RO ;

HAFNER, A ;

RIEDIKER, M .

PURE AND APPLIED CHEMISTRY, 1990, 62 (04) :631-642

[9] OPTICAL-ACTIVITY OF 2.2'-SPIROBIINDANE-1.1'-DIONE .4. OPTICALLY-ACTIVE, AROMATIC SUBSTITUTED SPIRANS [J].

FALK, H ;

FROSTL, W ;

HOFER, O ;

SCHLOGL, K .

MONATSHEFTE FUR CHEMIE, 1974, 105 (03) :598-610

[10] OPTICALLY-ACTIVE, AROMATICALLY SUBSTITUTED SPIRANES .3. PREPARATION, ABSOLUTE-CONFIGURATION AND OPTICAL PURITY OF 2.2'-SPIRO-BIINDAN-1.1'-DIONE [J].

FALK, H ;

FROSTL, W ;

SCHLOGL, K .

MONATSHEFTE FUR CHEMIE, 1974, 105 (03) :574-597

← 1 2 3 4 →