SYNTHESIS AND STEREOCHEMISTRY OF ALLENES .3. HIGHLY STEREOSELECTIVE SYNTHESIS OF CHIRAL ALKYLALLENES BY ORGANOCOPPER(I)-INDUCED ANTI 1,3-SUBSTITUTION OF CHIRAL PROPYNYL ESTERS

被引:90
作者
ELSEVIER, CJ [1 ]
VERMEER, P [1 ]
机构
[1] UNIV AMSTERDAM,ANORGAN CHEM LAB,1018 WV AMSTERDAM,NETHERLANDS
关键词
D O I
10.1021/jo00276a040
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
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页码:3726 / 3730
页数:5
相关论文
共 51 条
[1]   METAL CATALYSIS IN ORGANIC-REACTIONS .18. STEREOCHEMISTRY OF THE TRANSITION-METAL CATALYZED CROSS-COUPLING OF "(S)-1-BROMO-3-METHYL-1,2-PENTADIENE WITH ISOBUTYLMETAL COMPOUNDS [J].
CAPORUSSO, AM ;
LARDICCI, L ;
DASETTIMO, F .
TETRAHEDRON LETTERS, 1986, 27 (09) :1067-1068
[2]   REACTIONS OF 3-ALKYL-1-BROMOALLENES AND 3,3-DIALKYL-1-BROMOALLENES WITH ORGANOCUPRATES - EFFECTS OF THE NATURE OF THE CUPRATE REAGENT ON THE REGIOSELECTIVITY AND STEREOSELECTIVITY [J].
CAPORUSSO, AM ;
POLIZZI, C ;
LARDICCI, L .
TETRAHEDRON LETTERS, 1987, 28 (48) :6073-6076
[3]  
CAPORUSSO AM, 1988, GAZZ CHIM ITAL, V118, P857
[4]   CHIRAL ALLENES ARE RACEMIZED BY ORGANOCUPRATES [J].
CLAESSON, A ;
OLSSON, LI .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1979, (12) :524-525
[5]   STEREOCHEMISTRY OF THE SN2' DISPLACEMENT OF CHIRAL 1,3-DISUBSTITUTED BROMOALLENES TO FORM CHIRAL ACETYLENES [J].
COREY, EJ ;
BOAZ, NW .
TETRAHEDRON LETTERS, 1984, 25 (29) :3059-3062
[6]   OPTICAL ACTIVITY AND ABOLUTE CONFIGURATION OF CHIRAL ALLENES [J].
CRABBE, P ;
VELARADE, E ;
ANDERSON, HW ;
CLARK, SD ;
MOORE, WR ;
DRAKE, AF ;
MASON, SF .
JOURNAL OF THE CHEMICAL SOCIETY D-CHEMICAL COMMUNICATIONS, 1971, (20) :1261-&
[7]   SYNTHETIC USE OF AN UNUSUAL ORGANOCUPRATE INTERMEDIATE [J].
DOLLAT, JM ;
LUCHE, JL ;
CRABBE, P .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1977, (21) :761-762
[8]  
ELSEVIER CJ, 1985, ISRAEL J CHEM, V26, P174
[9]   THE MOLECULAR-STRUCTURE OF ALLENES AND KETENES .17. EXCITED-STATES OF THE ALLENE CHROMOPHORE - PHOTOELECTRON, CIRCULAR-DICHROISM, AND ABSORPTION-SPECTROSCOPY OF ALKYLGENOALLENE AND HALOGENOALLENE [J].
ELSEVIER, CJ ;
VERMEER, P ;
GEDANKEN, A ;
RUNGE, W .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (08) :2537-2547
[10]   ANTI STEREOSELECTIVITY IN THE PALLADIUM(0)-CATALYZED CONVERSION OF PROPARGYLIC ESTERS INTO ALLENES BY PHENYLZINC CHLORIDE [J].
ELSEVIER, CJ ;
STEHOUWER, PM ;
WESTMIJZE, H ;
VERMEER, P .
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (07) :1103-1105