N-heterocyclic carbene catalyzed ring expansion of 4-formyl-β-lactams:: Synthesis of succinimide derivatives

被引：101
作者：
Li, Gong-Qiang [1 ]
Li, Yi [1 ]
Dai, Li-Xin [1 ]
You, Shu-Li [1 ]
机构：
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 200032, Peoples R China
来源：
ORGANIC LETTERS | 2007年 / 9卷 / 18期
关键词：
D O I：
10.1021/ol0713537
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
N-Heterocyclic carbene (NHC) has been employed as an efficient catalyst for ring expansion of 4-formyl-beta-lactams, allowing the facile synthesis of succinimide derivatives. This organocatalytic process features readily availability of the catalyst, low catalyst loading, and mild reaction conditions.
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收藏
页码：3519 / 3521
页数：3
相关论文
共 57 条
[1]   Synthesis and X-ray crystallographic structure of leucine-phenylalanyl succinimide-based pseudopeptides [J].
Abell, AD ;
Oldham, MD .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (05) :1509-1513
[2]   Organocatalytic ring expansion of β-lactams to γ-lactams through a novel N1-C4 bond cleavage.: Direct svnthesis of enantiopure succinimide derivatives [J].
Alcaide, B ;
Almendros, P ;
Cabrero, G ;
Ruiz, MP .
ORGANIC LETTERS, 2005, 7 (18) :3981-3984
[3]   Novel N1-C4 β-lactam bond breakage.: Synthesis of enantiopure α-alkoxy-γ-keto acid derivatives [J].
Alcaide, B ;
Almendros, P ;
Redondo, MC .
ORGANIC LETTERS, 2004, 6 (11) :1765-1767
[4]  
Alcaide B, 2002, SYNLETT, P381
[5]   4-Oxoazetidine-2-carbaldehydes as useful building blocks in stereocontrolled synthesis [J].
Alcaide, B ;
Almendros, P .
CHEMICAL SOCIETY REVIEWS, 2001, 30 (04) :226-240
[6]   Methyllycaconitine analogues have mixed antagonist effects at nicotinic acetylcholine receptors [J].
Barker, D ;
Lin, DHS ;
Carland, JE ;
Chu, CPY ;
Chebib, M ;
Brimble, MA ;
Savage, GP ;
McLeod, MD .
BIOORGANIC & MEDICINAL CHEMISTRY, 2005, 13 (14) :4565-4575
[7]  
BHATTI BS, 2006, Patent No. 06023630
[8]   ON THE MECHANISM OF THIAMINE ACTION .4. EVIDENCE FROM STUDIES ON MODEL SYSTEMS [J].
BRESLOW, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1958, 80 (14) :3719-3726
[9]   Regioselective reductions of various 3-aminosuccinimides; Application to the synthesis of two heterocyclic systems. [J].
Briere, JF ;
Charpentier, P ;
Dupas, G ;
Queguiner, G ;
Bourguignon, J .
TETRAHEDRON, 1997, 53 (06) :2075-2086
[10]  
BURSTEIN C, 2004, ANGEW CHEM INT EDIT, V43, P6025
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