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
来源：
ORGANIC LETTERS | 2006年 / 8卷 / 14期
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.
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收藏
页码：3041 / 3043
页数：3
相关论文
共 23 条
[11]   Synthesis of new potential aminopeptidase inhibitors by Lewis acid induced rearrangement of 2,3-epoxy amines and regiospecific nucleophilic trapping of aziridinium ion intermediates with alpha-amino esters. [J].
Liu, QY ;
Marchington, AP ;
Rayner, CM .
TETRAHEDRON, 1997, 53 (46) :15729-15742
[12]   Stereoselective ring opening of meso bicyclic hydrazines: A straightforward approach to hydrazino cyclopentenic cores [J].
Luna, AP ;
Cesario, M ;
Bonin, M ;
Micouin, L .
ORGANIC LETTERS, 2003, 5 (25) :4771-4774
[13]   Enantio selective desymmetrization of meso bicyclic hydrazines: A novel approach to the asymmetric synthesis of polysubstituted amino cyclopentanic cores [J].
Luna, AP ;
Ceschi, MA ;
Bonin, M ;
Micouin, L ;
Husson, HP ;
Gougeon, S ;
Estenne-Bouhtou, G ;
Marabout, B ;
Sevrin, M ;
George, P .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (10) :3522-3524
[14]   Reversal of enantioselectivity in the asymmetric rhodium- versus iridium-catalyzed hydroboration of meso substrates [J].
Luna, AP ;
Bonin, M ;
Micouin, L ;
Husson, HP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (41) :12098-12099
[15]   7-substituted 2-azabicyclo[2.2.1]heptanes as key intermediates for the synthesis of novel epibatidine analogues;: synthesis of syn- and anti-isoepiboxidine [J].
Malpass, JR ;
White, R .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (16) :5328-5334
[16]   THE USE OF DIETHYL AZODICARBOXYLATE AND TRIPHENYLPHOSPHINE IN SYNTHESIS AND TRANSFORMATION OF NATURAL-PRODUCTS [J].
MITSUNOBU, O .
SYNTHESIS-STUTTGART, 1981, (01) :1-28
[17]   SIGMA-BRIDGED 2-NORBORNYL CATION AND ITS SIGNIFICANCE TO CHEMISTRY [J].
OLAH, GA .
ACCOUNTS OF CHEMICAL RESEARCH, 1976, 9 (02) :41-52
[18]   REACTION OF N-SUBSTITUTED 1,2,4-TRIAZOLINE-3,5-DIONES AND TRANS-CYCLOOCTENE - DIRECT OBSERVATION OF AN AZIRIDINIUM IMIDE [J].
POON, THW ;
PARK, SH ;
ELEMES, Y ;
FOOTE, CS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (42) :10468-10473
[19]   HETEROATOM PARTICIPATION DURING ADDITION-REARRANGEMENT REACTIONS OF 2-THIANORBORNENE AND 2-AZANORBORNENES [J].
RAASCH, MS .
JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (02) :161-172
[20]   REACTION OF EXO-NORBORNYLENE OXIDE WITH HYDROGEN BROMIDE [J].
WALBORSKY, HM ;
LONCRINI, DF .
JOURNAL OF ORGANIC CHEMISTRY, 1957, 22 (09) :1117-1117
123