ENANTIOSELECTIVE SYNTHESIS OF SPIRO[4.4]NON- AND SPIRO[4.5]DEC-2-ENE-1,6-DIONES

被引:22
作者
CHITKUL, B
PINYOPRONPANICH, Y
THEBTARANONTH, C
THEBTARANONTH, Y
TAYLOR, WC
机构
[1] MAHIDOL UNIV,FAC SCI,DEPT CHEM,BANGKOK 10400,THAILAND
[2] UNIV SYDNEY,DEPT ORGAN CHEM,SYDNEY,NSW 2006,AUSTRALIA
关键词
D O I
10.1016/S0040-4039(00)79975-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Spiro[4.4]non- and spiro[4.5]dec-2-ene-1,6-diones [2; n = 0 and 1] were prepared in moderate to high enantiomeric purities via asymmetric allylation of enamines 6 and ketal derivatives 7 and 8 formed from keto-esters 5, followed by a carbanionic cyclization process.
引用
收藏
页码:1099 / 1102
页数:4
相关论文
共 14 条
[1]   STEREOSELECTIVE REACTIONS .21. ASYMMETRIC ALKYLATION OF ALPHA ALKYL BETA-KETO-ESTERS TO ALPHA,ALPHA-DIALKYL BETA-KETO-ESTERS HAVING EITHER (R)-CHIRAL OR (S)-CHIRAL QUATERNARY CENTER DEPENDING ON THE SOLVENT SYSTEM [J].
ANDO, K ;
TAKEMASA, Y ;
TOMIOKA, K ;
KOGA, K .
TETRAHEDRON, 1993, 49 (08) :1579-1588
[2]   SYNTHETIC STUDIES ON HISTRIONICOTOXINS .1. STEREOCONTROLLED SYNTHESIS OF (+ OR -)-PERHYDROHISTRIONICOTOXIN [J].
ARATANI, M ;
DUNKERTON, LV ;
FUKUYAMA, T ;
KISHI, Y ;
KAKOI, H ;
SUGIURA, S ;
INOUE, S .
JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (13) :2009-2011
[3]   LEWIS ACID-CATALYZED REARRANGEMENTS OF STRUCTURALLY RELATED ALPHA,BETA-UNSATURATED EPOXY KETONES AND OXIMES - A COMPLEMENTARY APPROACH TO THE SYNTHESIS OF ISOMERIC 1,4-DIKETOSPIRO[NORMAL,META] ALKANES [J].
BACH, RD ;
TUBERGEN, MW ;
KLIX, RC .
TETRAHEDRON LETTERS, 1986, 27 (31) :3565-3568
[4]   FACILE SYNTHESIS OF 1-AZOSPIRO(5.5)UNDECAN-2,7-DIONE [J].
BOND, FT ;
STEMKE, JE ;
POWELL, DW .
SYNTHETIC COMMUNICATIONS, 1975, 5 (06) :427-433
[5]   CHIRALITY AS A PROBE IN BETA-KETO ESTER TAUTOMERISM [J].
DECICCO, CP ;
BUCKLE, RN .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (03) :1005-1008
[6]   SYNTHESIS OF CHIRAL NONRACEMIC DIOLS VIA NUCLEOPHILIC OPENING OF (S,S)-1,2,3,4-DIEPOXYBUTANE [J].
DEVINE, PN ;
OH, T .
TETRAHEDRON LETTERS, 1991, 32 (07) :883-886
[7]  
Fr?ter G., 1980, HELV CHIM ACTA, V63, P1383
[8]   ASYMMETRIC NUCLEOPHILIC-ADDITION OF CHIRAL BETA-ENAMINO ESTERS TO ACRYLONITRILE [J].
GUINGANT, A ;
HAMMAMI, H .
TETRAHEDRON-ASYMMETRY, 1993, 4 (01) :25-26
[9]   ASYMMETRIC-SYNTHESIS CATALYZED BY CHIRAL FERROCENYLPHOSPHINE-TRANSITION-METAL COMPLEXES .5. PALLADIUM-CATALYZED ASYMMETRIC ALLYLATION OF ACTIVE METHINE COMPOUNDS [J].
HAYASHI, T ;
KANEHIRA, K ;
HAGIHARA, T ;
KUMADA, M .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (01) :113-120
[10]   APPLICATION OF CHIRAL CYCLIC DIOLS TO ASYMMETRIC ALKYLATION [J].
KATO, K ;
SUEMUNE, H ;
SAKAI, K .
TETRAHEDRON LETTERS, 1992, 33 (02) :247-250