First diastereoselective [3+2] cycloaddition of chiral non-racemic alkenyl Fischer carbene complexes with diazomethane derivatives

被引:30
作者
Barluenga, J
FernandezMari, F
Viado, AL
Aguilar, E
Olano, B
机构
[1] Instituto Universitario de Química Organometálica 'Enrique Moles', Unidad Asociada al C.S.I.C., Universidad de Oviedo, 33071 Oviedo, C/ Julián Clavería
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1997年 / 16期
关键词
D O I
10.1039/a704228k
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
(-)-8-Phenylmenthol derived pentacarbonylalkenyl(alkoxy)chromium carbene complexes react with diazomethane derivatives to give only one diastereomer of enantiomerically pure 4,5-dihydro-1H-pyrazoles; the one-pot synthesis of the corresponding esters is also described.
引用
收藏
页码:2267 / 2268
页数:2
相关论文
共 12 条
[1]   1,3-DIPOLAR CYCLOADDITION REACTIONS OF ALKENYLALKOXYCARBENE CHROMIUM COMPLEXES [J].
BALDOLI, C ;
DELBUTTERO, P ;
LICANDRO, E ;
MAIORANA, S ;
PAPAGNI, A ;
ZANOTTIGEROSA, A .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1994, 476 (02) :C27-C29
[2]  
BARLUENGA J, 1994, ANGEW CHEM INT EDIT, V33, P1392, DOI 10.1002/anie.199413921
[3]   UNEXPECTED AND EASY ANNULATION OF FISCHER-TYPE PHENYLETHENYL CARBENE COMPLEXES [J].
BARLUENGA, J ;
AZNAR, F ;
BARLUENGA, S .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (19) :1973-1974
[4]   ASYMMETRIC SYN-SELECTIVE MICHAEL ADDITION OF ENOLATES TO CHIRAL 8-PHENYLMENTHYLOXY VINYL CHROMIUM CARBENE COMPLEXES [J].
BARLUENGA, J ;
MONTSERRAT, JM ;
FLOREZ, J ;
GARCIAGRANDA, S ;
MARTIN, E .
CHEMISTRY-A EUROPEAN JOURNAL, 1995, 1 (04) :236-242
[5]   ASYMMETRIC EXO-SELECTIVE DIELS-ALDER REACTIONS OF CYCLIC BF2 ADDUCTS OF FUNCTIONALIZED FISCHER VINYLCARBENE COMPLEXES WITH CHIRAL 2-AMINO-1,3-DIENES [J].
BARLUENGA, J ;
CANTELI, RM ;
FLOREZ, J ;
GARCIAGRANDA, S ;
GUTIERREZRODRIGUEZ, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (15) :6949-6950
[6]   First [4+2] cycloaddition of alkynyl Fischer carbene complexes with heterodienes. Facile synthesis of 1,4-dihydropyridines from 1-azadienes [J].
Barluenga, J ;
Tomas, M ;
LopezPelegrin, JA ;
Rubio, E .
TETRAHEDRON LETTERS, 1997, 38 (22) :3981-3984
[7]   1,3-DIPOLAR CYCLOADDITION REACTIONS OF TRANSITION-METAL CARBENE COMPLEXES AND THE FORMAL [3 + 2 + 1] PYRIDINANNULATION OF THE CYCLOADDUCTS [J].
CHAN, KS ;
WULFF, WD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (17) :5229-5236
[8]   1,3-DIPOLAR CYCLOADDITIONS OF ALKYNYL FISCHER CARBENE COMPLEXES WITH NITRONES [J].
CHAN, KS .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (10) :2602-2603
[9]   CHROMIUM AND TUNGSTEN PENTACARBONYL GROUPS AS REACTIVITY AND SELECTIVITY AUXILIARIES IN [3+2] CYCLOADDITION OF ALKYNYL FISCHER CARBENE COMPLEXES WITH N-ALKYL NITRONES [J].
CHAN, KS ;
YEUNG, ML ;
CHAN, WK ;
WANG, RJ ;
MAK, TCW .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (06) :1741-1747
[10]   HETEROANNULATION OF ALKYNYL CARBENE COMPLEXES - [3+2] DIPOLAR CYCLOADDITION OF PENTACARBONYL-[(ALKYNYL)(METHOXY)CARBENE]METALS WITH MASKED 1,3-DIPOLES [J].
CHOI, YH ;
KANG, BS ;
YOON, YJ ;
KIM, JN ;
SHIN, SC .
SYNTHETIC COMMUNICATIONS, 1995, 25 (14) :2043-2050