Highly regio- and diastereoselective palladium-catalyzed allylic substitution. Synthesis of 3-(2-aminobutylidene)-4-arylazetidin-2-ones

被引：10
作者：
Cardillo, G [1 ]
Fabbroni, S [1 ]
Gentilucci, L [1 ]
Perciaccante, R [1 ]
Tolomelli, A [1 ]
机构：
[1] Univ Bologna, Dipartimento Chim G Ciamician, I-40126 Bologna, Italy
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2005年 / 347卷 / 06期
关键词：
allylic substitution; azetidinone; diastereoselectivity; palladium; regioselectivity;
D O I：
10.1002/adsc.200404385
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
The palladium-catalyzed benzylamine attack to a particular allylic moiety, the 3-alkenyl-3-bromoazetidin-2-one is herein reported. This reaction shows interesting mechanistic aspects and allows us to introduce in one step and under high regio- and stereocontrol the amino function in the C3 side chain of non-conventional beta-lactams, thus offering the opportunity for designing new potential glutamine syntethase inhibitors, such as Tabtoxin analogues.
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收藏
页码：833 / 838
页数：6
相关论文
共 60 条
[11]   Highly diastereoselective allylic azide formation and isomerization.: Synthesis of 3(2′-amino)-β-lactams [J].
Cardillo, G ;
Fabbroni, S ;
Gentilucci, L ;
Perciaccante, R ;
Piccinelli, F ;
Tolomelli, A .
ORGANIC LETTERS, 2005, 7 (04) :533-536
[12]   Practical synthesis of 3-bromo-5,6-dihydropyridin-2-ones via β,γ-unsaturated α-bromo-ketene/imine cycloaddition [J].
Cardillo, G ;
Fabbroni, S ;
Gentilucci, L ;
Perciaccante, R ;
Piccinelli, F ;
Tolomelli, A .
TETRAHEDRON, 2004, 60 (23) :5031-5040
[13]   α-Bromo-β,γ-unsaturated ketenes for the synthesis of α-benzylamino-β,γ-unsaturated acids [J].
Cardillo, G ;
Fabbroni, S ;
Gentilucci, L ;
Perciaccante, R ;
Tolomelli, A .
TETRAHEDRON-ASYMMETRY, 2004, 15 (04) :593-601
[14]   Enantioselective synthesis of aziridine 2,2-dicarboxylates. Part 1: Copper(II)-bisoxazoline complex-catalysed Michael reaction on alkylidene malonates [J].
Cardillo, G ;
Fabbroni, S ;
Gentilucci, L ;
Gianotti, M ;
Perciaccante, R ;
Tolomelli, A .
TETRAHEDRON-ASYMMETRY, 2002, 13 (13) :1407-1410
[15]   Enantioselective synthesis of aziridine 2,2-dicarboxylates. Part 2: Determination of the absolute configuration [J].
Cardillo, G ;
Fabbroni, S ;
Gentilucci, L ;
Gianotti, M ;
Perciaccante, R ;
Selva, S ;
Tolomelli, A .
TETRAHEDRON-ASYMMETRY, 2002, 13 (13) :1411-1415
[16]   Conjugate addition of hydroxylamino derivatives to alkylidene malonates in the presence of chiral Lewis acids [J].
Cardillo, G ;
Gentilucci, L ;
Gianotti, M ;
Kim, H ;
Perciaccante, R ;
Tolomelli, A .
TETRAHEDRON-ASYMMETRY, 2001, 12 (17) :2395-2398
[17]   Synthesis of aziridine-2,2-dicarboxylates via 1,4-addition of N,O-(bistrimethylsilyl)hydroxylamine to α,β-unsaturated malonates [J].
Cardillo, G ;
Gentilucci, L ;
Gianotti, M ;
Perciaccante, R ;
Tolomelli, A .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (25) :8657-8660
[18]   NMR investigations on boron complexes in the conjugate addition on α,β-unsaturated imides [J].
Cardillo, G ;
Gentilucci, L ;
Gianotti, M ;
Tolomelli, A .
ORGANIC LETTERS, 2001, 3 (08) :1165-1167
[19]  
Cardillo G, 1999, SYNLETT, P1727
[20]   Synthesis of enantiomerically pure trans aziridine-2-carboxylates by diastereoselective Gabriel-Cromwell reaction [J].
Cardillo, G ;
Gentilucci, L ;
Tomasini, C ;
CastejonBordas, MPV .
TETRAHEDRON-ASYMMETRY, 1996, 7 (03) :755-762
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