REGIOCHEMISTRY AND STEREOCHEMISTRY OF THE COUPLING OF PHENYLTHIOPENTADIENYL METALS WITH C-ELECTROPHILES

被引:8
作者
FLORIO, S
RONZINI, L
SGARRA, R
机构
[1] Laboratorio di Chimica Organica, Dipartimento di Biologia, Universitá di Lecce, 73100 Lecce, Via Monteroni
关键词
D O I
10.1016/0040-4039(90)80219-C
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Phenylthiopentadienyl anions 2 couple with MeI and cyclopentanone either regioselectively and stereoselectively to give 3a and 4a respectively. With aldehydes the regiochemistry and stereochemistry is affected by the counterion of 2, furnishing α-, γ- or ε-regioisomeric alchools. © 1990.
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收藏
页码:2327 / 2330
页数:4
相关论文
共 10 条
[1]  
ATLANI PM, 1974, TETRAHEDRON LETT, P2665
[2]   DECOMPOSITION OF ARILAZIDES AND PARA-TOSYLAZIDE BY THF NORMAL-BUTYLLITHIUM - A NEW SOURCE OF DIAZOMETHANE [J].
BABUDRI, F ;
DINUNNO, L ;
FLORIO, S ;
VALZANO, S .
TETRAHEDRON, 1984, 40 (10) :1731-1736
[3]  
BIELLMANN JF, 1982, ORG REACTIONS, V27, P1
[4]   HEXAMETHYLPHOSPHORAMIDE-MEDIATED CONJUGATE ADDITION OF (ALKYLTHIO)ALLYLLITHIUM (PHENYLTHIO)ALLYLLITHIUM AND (PHENYLSELENO)ALLYLLITHIUM REAGENTS TO 2-CYCLOPENTENONE [J].
BINNS, MR ;
HAYNES, RK .
JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (19) :3790-3795
[5]   REVERSIBLE ALLYLIC CONDENSATION OF METALLOALLYLS OF HETEROCYCLES - COUNTERION EFFECT [J].
EPIFANI, E ;
FLORIO, S ;
INGROSSO, G .
TETRAHEDRON, 1988, 44 (18) :5869-5877
[6]   REGIOSELECTIVE CONTROL OF ALLYLLITHIUMS OF SOME HETEROCYCLES - ALPHA-VS-GAMMA CONDENSATION WITH ALDEHYDES [J].
EPIFANI, E ;
FLORIO, S ;
INGROSSO, G .
TETRAHEDRON LETTERS, 1987, 28 (50) :6385-6388
[7]   A GENERAL-APPROACH TO THE SYNTHESIS OF MONO-OLEFINIC INSECT SEX-PHEROMONES OF Z-CONFIGURATION OR E-CONFIGURATION [J].
FIANDANESE, V ;
MARCHESE, G ;
NASO, F ;
RONZINI, L .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (06) :1115-1119
[8]   NEW REAGENTS .36. REACTIONS OF ORGANOELEMENT-SUBSTITUTED PENTADIENE - COMPLEXATION WITH TRANSITION-METALS AND PREPARATIVE APPLICATION OF LITHIATION PRODUCTS [J].
KAUFFMANN, T ;
GAYDOUL, KR .
TETRAHEDRON LETTERS, 1985, 26 (34) :4071-4074
[9]  
SLOTTER PL, 1973, J AM CHEM SOC, V95, P4444
[10]   INFLUENCE OF ELECTROPHILES ON REGIOSELECTIVE ALKYLATION OF AMBIDENT CARBANION FROM DIHYDROTHIOPYRAN [J].
TORII, S ;
TANAKA, H ;
TOMOTAKI, Y .
CHEMISTRY LETTERS, 1974, (12) :1541-1542