Skeletal rearrangements in the 2,3-diazanorbornene series. A fast access to highly functionalized cyclopentanes

被引:30
作者
Bournaud, Chloee
Bonin, Martine
Micouin, Laurent
机构
[1] Associee CNRS, UMR 8638, Chim Therapeut Lab, F-75270 Paris 06, France
[2] Univ Paris 05, Fac Sci Pharmaceut & Biol, F-75270 Paris 06, France
关键词
D O I
10.1021/ol060972x
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] Acid-catalyzed nucleophilic substitution of bicyclic hydrazine-epoxide involves nitrogen participation, leading to a skeletal rearrangement. This transformation enables the fast preparation of disubstituted bicyclic hydrazines in a regio-and stereoselective manner, leading to several polyfunctional diaminocyclopentanes after hydrogenolysis.
引用
收藏
页码:3041 / 3043
页数:3
相关论文
共 23 条
[1]   2,3-DIAZABICYCLO[2.2.1]HEPTYL RING SYSTEM .I. SYNTHESIS AND CHARACTERIZATION OF SOME 5-SUBSTITUTED DERIVATIVES [J].
ALLRED, EL ;
ANDERSON, CL ;
SMITH, RL .
JOURNAL OF ORGANIC CHEMISTRY, 1966, 31 (11) :3493-&
[2]  
[Anonymous], 2005, COMPREHENSIVE ORGANI
[3]   Fluorinated alcohols:: A new medium for selective and clean reaction [J].
Bégué, JP ;
Bonnet-Delpon, D ;
Crousse, B .
SYNLETT, 2004, (01) :18-29
[4]   Highly functionalized cyclopentanes from meso bicyclic hydrazines. A rapid access to mannosidase inhibitors [J].
Bournaud, C ;
Robic, D ;
Bonin, M ;
Micouin, L .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (08) :3316-3317
[5]  
Cossy J., 2002, TARGETS HETEROCYCL S, V6, P1
[6]  
Dahanukar VH, 2002, CURR OPIN DRUG DISC, V5, P918
[7]   Ring enlargement of polyhydroxylated pyrrolidines to piperidines by Mitsunobu reaction: A fortuitous synthesis of 1-deoxy-L-allonojirimycin [J].
Dondoni, A ;
Richichi, B ;
Marra, A ;
Perrone, D .
SYNLETT, 2004, (10) :1711-1714
[8]   Synthesis and reactivity of mixed alkynylalanes by direct triethylamine-catalyzed alumination of terminal alkynest [J].
Feuvrie, C ;
Blanchet, J ;
Bonin, M ;
Micouin, L .
ORGANIC LETTERS, 2004, 6 (14) :2333-2336
[9]   THE MITSUNOBU REACTION OF SOME INDAN AMINO-ALCOHOLS [J].
FREEDMAN, J ;
VAAL, MJ ;
HUBER, EW .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (02) :670-672
[10]   Regio- and stereoselective ring opening reaction of 2,3-epoxy amines with organo-aluminum reagents leading to 2-substituted 3-amino alcohols [J].
Liu, CQ ;
Hashimoto, Y ;
Saigo, K .
TETRAHEDRON LETTERS, 1996, 37 (34) :6177-6180