INTRAMOLECULAR MITSUNOBU DISPLACEMENT WITH CARBON NUCLEOPHILES - PREPARATION OF ALPHA-NITROCYCLOPROPANES

被引:29
作者
YU, JR
FALCK, JR
MIOSKOWSKI, C
机构
[1] UNIV TEXAS,SW MED CTR,DEPT MOLEC GENET,DALLAS,TX 75235
[2] UNIV LOUIS PASTEUR,FAC PHARM,SYNTH BIOORG LAB,CNRS,URA 1386,F-67401 ILLKIRCH GRAFFENS,FRANCE
[3] UNIV TEXAS,SW MED CTR,DEPT PHARMACOL,DALLAS,TX 75235
关键词
D O I
10.1021/jo00040a004
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Gamma-nitroalkanols are converted to alpha-nitrocyclopropanes with inversion of configuration in good to excellent yields using diethyl azodicarboxylate and Ph3P.
引用
收藏
页码:3757 / 3759
页数:3
相关论文
共 32 条
[1]   EQUILIBRIUM ACIDITIES OF CARBON ACIDS [J].
BORDWELL, FG .
PURE AND APPLIED CHEMISTRY, 1977, 49 (07) :963-968
[2]   STEREOCHEMISTRY AND MECHANISM OF CYCLOPROPANE FORMATION FROM IONIZATION OF C5H5(CO)2FE(CH2)3X [J].
CASEY, CP ;
VOSEJPKA, LJS .
ORGANOMETALLICS, 1992, 11 (02) :738-744
[3]   CARBOHYDRATES AS CHIRAL AUXILIARIES - ASYMMETRIC CYCLOPROPANATION REACTION OF ACYCLIC OLEFINS [J].
CHARETTE, AB ;
COTE, B ;
MARCOUX, JF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (21) :8166-8167
[4]   TOTAL SYNTHESIS OF DL-SIRENIN [J].
COREY, EJ ;
ACHIWA, K ;
KATZENEL.JA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1969, 91 (15) :4318-&
[5]  
ELLIOTT M, 1977, ACS S SERIES, V87
[6]  
FONTANI P, 1991, SYNTHESIS-STUTTGART, P605
[7]   HYBRIDALACTONE, AN UNUSUAL FATTY-ACID METABOLITE FROM THE RED ALGA LAURENCIA-HYBRIDA (RHODOPHYTA, RHODOMELACEAE) [J].
HIGGS, MD ;
MULHEIRN, LJ .
TETRAHEDRON, 1981, 37 (24) :4259-4262
[8]   STRUCTURE, SYNTHESIS, AND PROPERTIES OF SOME PERSUBSTITUTED 1,2-DINITROETHANES - IN QUEST OF NITROCYCLOPROPYL-ANION DERIVATIVES [J].
KAI, Y ;
KNOCHEL, P ;
KWIATKOWSKI, S ;
DUNITZ, JD ;
OTH, JFM ;
SEEBACH, D ;
KALINOWSKI, HO .
HELVETICA CHIMICA ACTA, 1982, 65 (01) :137-161
[9]   MARINE STEROLS [J].
KERR, RG ;
BAKER, BJ .
NATURAL PRODUCT REPORTS, 1991, 8 (05) :465-497
[10]   5-MEMBERED, 4-MEMBERED, AND 3-MEMBERED CARBOCYCLIC RINGS FROM 2-DEOXYRIBOSE BY INTRAMOLECULAR NUCLEOPHILIC DISPLACEMENT REACTION [J].
KROHN, K ;
BORNER, G .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (21) :6038-6043