UNEXPECTED CIS OPENINGS OF CYCLOPENTADIENE MONOEPOXIDE WITH LITHIUM ACETYLIDES AND DIALKYLALKYNYLALANES

被引:6
作者
BRIGGS, AJ [1 ]
WALKER, KAM [1 ]
机构
[1] SYNTEX INC,INST ORGAN CHEM,PALO ALTO,CA 94304
关键词
D O I
10.1021/jo00296a076
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The reactions of vinyloxiranes with organometallic compounds have received considerable attention recently,conditions (n-BuLi/hexane) to the silyl-protected acetylide 2b, we were surprised to obtain exclusively the cis-1,4-opening product 5b (in 25% yield)7 rather than the expected trans-1,2-opening product 3b. © 1990, American Chemical Society. All rights reserved.
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页码:2962 / 2964
页数:3
相关论文
共 28 条
[1]   PYROLYSIS OF BETA-HYDROXYOLEFINS .3. A NOVEL METHOD FOR EXTENDING CARBON CHAINS [J].
ARNOLD, RT ;
SMOLINSKY, G .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1960, 82 (18) :4918-4920
[2]   SYNTHESIS OF RING HALOGENATED PROSTAGLANDINS [J].
ARRONIZ, CE ;
GALLINA, J ;
MARTINEZ, E ;
MUCHOWSKI, JM ;
VELARDE, E .
PROSTAGLANDINS, 1978, 16 (01) :47-65
[3]  
BOSE AK, 1973, TETRAHEDRON LETT, P1619
[4]   SYNTHESIS OF ANALOGS OF PROSTACYCLIN CONTAINING A THIAZOLE RING [J].
BRADBURY, RH ;
WALKER, KAM .
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (10) :1741-1750
[5]  
CHRISTL M, 1971, J AM CHEM SOC, V93, P3463, DOI 10.1021/ja00743a028
[6]   C-13 NUCLEAR MAGNETIC-RESONANCE SPECTRA OF PROSTAGLANDINS AND SOME PROSTAGLANDIN ANALOGS - (PULSED FOURIER-TRANSFORM MODE) [J].
COOPER, GF ;
FRIED, J .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1973, 70 (05) :1579-1584
[7]   SOLVENT MEDIATED REACTIONS OF DIETHYLHEX-1-YNYLALUMINIUM WITH 3,4-EPOXYCYCLOPENTENE [J].
CROSBY, GA ;
STEPHENSON, RA .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1975, (08) :287-288
[8]   MECHANISM AND SYNTHETIC UTILITY OF BORON-TRIFLUORIDE ETHERATE PROMOTED ORGANO-LITHIUM ADDITIONS [J].
EIS, MJ ;
WROBEL, JE ;
GANEM, B .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (12) :3693-3694
[9]   STUDIEN IN DER VITAMIN D-REIHE .14. EIN NEUER WEG ZU RING-A-BAUSTEINEN FUR DIE SYNTHESE VON 9.10-SECO-STEROIDEN [J].
INHOFFEN, HH ;
WEISSERMEL, K ;
QUINKERT, G ;
BARTLING, D .
CHEMISCHE BERICHTE-RECUEIL, 1956, 89 (04) :853-861
[10]   POTENT PROSTACYCLIN ANALOGS BASED ON THE BICYCLO[4.2.0]OCTANE RING-SYSTEM [J].
KLUGE, AF ;
KERTESZ, DJ ;
OYANG, C ;
WU, HY .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (13) :2860-2868