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 26 条

[1] A New Tandem Cross Metathesis-Intramolecular Aza-Michael Reaction for the Synthesis of α,α-Difluorinated Lactams
Fustero, Santos
Baez, Claribel
Sanchez-Rosello, Maria
Asensio, Amparo
Miro, Javier
del Pozo, Carlos
SYNTHESIS-STUTTGART, 2012, 44 (12): : 1863 - 1873
[2] Tandem Nucleophilic Addition-Intramolecular Aza-Michael Reaction: Facile Synthesis of Chiral Fluorinated Isoindolines
Fustero, Santos
Moscardo, Javier
Sanchez-Rosello, Maria
Rodriguez, Elsa
Barrio, Pablo
ORGANIC LETTERS, 2010, 12 (23) : 5494 - 5497
[3] Synthesis of substituted piperidines by enantioselective desymmetrizing intramolecular aza-Michael reactions
Guerola, Marta
Escolano, Marcos
Alzuet-Pina, Gloria
Gomez-Bengoa, Enrique
Ramirez de Arellano, Carmen
Sanchez-Rosello, Maria
del Pozo, Carlos
ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (25) : 4650 - 4658
[4] The intramolecular aromatic nucleophilic substitution as a route to tricyclic β-lactams.: Synthesis of the novel 4-oxa-7-azabicyclo[4.2.0] octane skeleton
Del Buttero, P
Molteni, G
Papagni, A
Pilati, T
TETRAHEDRON, 2003, 59 (28) : 5259 - 5263
[5] Diastereodivergent Synthesis of Chiral Tetrahydropyrrolodiazepinediones via a One-Pot Intramolecular aza-Michael/Lactamization Sequence
Chennamadhavuni, Spandan
Panek, James S.
Porco, John A., Jr.
Brown, Lauren E.
JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (24): : 15449 - 15462
[6] Enantioselective synthesis of 2-substituted pyrrolidines via domino cross metathesis/intramolecular aza-Michael addition
Liu, Hanbin
Zeng, Chuanqi
Guo, Jiajia
Zhang, Mengyao
Yu, Shouyun
RSC ADVANCES, 2013, 3 (06): : 1666 - 1668
[7] Tandem aza-Michael/spiro-ring closure sequence: access to a versatile scaffold and total synthesis of (±)-coerulescine
Goermen, Meral
Le Goff, Ronan
Lawson, Ata Martin
Daich, Adam
Comesse, Sebastien
TETRAHEDRON LETTERS, 2013, 54 (17) : 2174 - 2176
[8] Enantioselective synthesis of 3-substituted 1,2-oxazinanes via organocatalytic intramolecular aza-Michael addition
Cheng, Shuanghua
Yu, Shouyun
ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (43) : 8607 - 8610
[9] Synthesis of 3-substituted quinolines by ruthenium-catalyzed aza-Michael addition and intramolecular annulation of enaminones with anthranils
Yan, Kelu
Liu, Min
Wen, Jiangwei
Liu, Xiao
Wang, Xiaoyu
Sui, Xinlei
Shang, Wenda
Wang, Xiu
NEW JOURNAL OF CHEMISTRY, 2022, 46 (16) : 7329 - 7333
[10] Synthesis of 4-arylethyl-6-arylpyrimidine-2-thiols through aza-Michael addition/nucleophilic addition/aromatization tandem reactions
Li, Zheng
Song, Wenli
He, Jiaojiao
Du, Yan
Yang, Jingya
HETEROCYCLIC COMMUNICATIONS, 2018, 24 (01) : 23 - 26

← 1 2 3 →