New and expeditious tandem sequence aza-Michael/intramolecular nucleophilic substitution route to substituted γ-lactams:: Synthesis of the tricyclic core of (±)-martinellines

被引：76

作者：

Comesse, Sebastien ^{[1
]}

Sanselme, Morgane ^{[2
]}

Daich, Adam ^{[1
]}

机构：

[1] Univ Havre, UFR Sci & Tech, URCOM, EA 3221, F-76058 Le Havre, France

[2] Univ Rouen, UPRES EA, IRCOF 3233, F-76821 Mont St Aignan, France

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 73卷 / 14期

关键词：

D O I：

10.1021/jo702752w

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new and highly diastereoselective tandem reaction aza-Michael/intramolecular nucleophilic substitution is presented. This unprecedented tandem reaction between N-substituted alpha-bromoacetamides and Michael acceptors proceeds with good yields and excellent diastereoselectivity to provide the corresponding trisubstituted gamma-lactam systems. An application to the concise synthesis of the tricyclic core of martinelline alkaloids is also described.

引用

页码：5566 / 5569

页数：4

共 40 条

[1] Organocatalytic ring expansion of β-lactams to γ-lactams through a novel N1-C4 bond cleavage.: Direct svnthesis of enantiopure succinimide derivatives
Alcaide, B
Almendros, P
Cabrero, G
Ruiz, MP
[J]. ORGANIC LETTERS, 2005, 7 (18) : 3981 - 3984
[2] Allous I, 2008, LETT ORG CHEM, V5, P73
[3] Total synthesis of (-)-martinellic acid
Badarinarayana, Vivek
Lovely, Carl J.
[J]. TETRAHEDRON LETTERS, 2007, 48 (14) : 2607 - 2610
[4] Bradykinin antagonists: new opportunities
Bock, MG
Longmore, J
[J]. CURRENT OPINION IN CHEMICAL BIOLOGY, 2000, 4 (04) : 401 - 406
[5] Rh(II)-catalyzed intramolecular C-H insertion of diazo substrates in water: Scope and limitations
Candeias, Nuno R.
Gois, Pedro M. P.
Afonso, Carlos A. M.
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (15) : 5489 - 5497
[6] Ruthenium-catalyzed stereoselective intramolecular carbenoid C-H insertion for β- and γ-lactam formations by decomposition of α-diazoacetamides
Choi, MKW
Yu, WY
Che, CM
[J]. ORGANIC LETTERS, 2005, 7 (06) : 1081 - 1084
[7] Coppola G.M., 1987, ASYMMETRIC SYNTHESIS
[8] Highly diastereoselective addition of the lithium enolate of α-diazoacetoacetate to N-sulfinyl imines:: Enantioselective synthesis of 2-oxo and 3-oxo pyrrolidines
Dong, Changqing
Mo, Fanyang
Wang, Jianbo
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (05) : 1971 - 1974
[9] Free radical cyclizations involving nitrogen
Fallis, AG
Brinza, IM
[J]. TETRAHEDRON, 1997, 53 (52) : 17543 - 17594
[10] Synthesis of 5-(hydroxymethyl)pyrrolidin-2-ones by cyclization of amide dianions with epibromohydrin
Freifeld, Ilia
Armbrust, Holger
Langer, Peter
[J]. SYNTHESIS-STUTTGART, 2006, (11): : 1807 - 1810

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