Diastereoselective Aza-Baylis-Hillman Reactions: Synthesis of Chiral α-Allenylamines and 2-Azetines from Allenic Esters

被引：17

作者：

Santos, Bruna S. ^{[1
]}

Cardoso, Ana L. ^{[1
]}

Beja, Ana Matos ^{[2
]}

Silva, Manuela Ramos ^{[2
]}

Paixao, Jose A. ^{[2
]}

Palacios, Francisco ^{[3
]}

Pinho e Melo, Teresa M. V. D. ^{[1
]}

机构：

[1] Univ Coimbra, Dept Chem, P-3004535 Coimbra, Portugal

[2] Univ Coimbra, Dept Phys, P-3004516 Coimbra, Portugal

[3] Univ Basque Country, Fac Pharm, Dept Organ Chem 1, Vitoria 01080, Spain

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 2010卷 / 17期

关键词：

Allenes; Nitrogen heterocycles; Chiral auxiliaries; Diastereoselectivity; N-SULFONATED IMINES; DIELS-ALDER REACTIONS; REGIOSELECTIVE SYNTHESIS; CONJUGATE PHOSPHINYL; ACTIVATED OLEFINS; DERIVATIVES; 2H-AZIRINES; OXIDES; METHOXYALLENE; 3-PYRROLINES;

D O I：

10.1002/ejoc.200901415

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reactivity of allenic esters towards activated N-sulfonylimines in the presence of DABCO was explored. A formal [2+2] cycloaddition of benzyl buta-2,3-dienoate and N-arylidenebenzenesulfonamides yielded mainly 2-methyleneazetidines. Interestingly, a DABCO-catalysed reaction of 2,3-allenoates, bearing a chiral auxiliary on the ester moiety, with N-arylidenebenzenesulfonamides led to optically active aza-Baylis-Hillman products and 2-azetine derivatives.

引用

页码：3249 / 3256

页数：8

共 26 条

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BASAVAIAH, D
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[22] New efficient synthesis of 1H-pyrimido[2,1-b]quinazoline-2, 6-diones via a tandem aza-Wittig/nucleophilic addition/intramolecular cyclization/isomerization reaction starting from the Baylis-Hillman adducts
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[23] Synthesis of Angularly Fused Pyrrolo[3,2-c]quinoline Lactones and 4-Carboxy-3-vinyl-1,2-dihydroquinolin-2-ones from Morita-Baylis-Hillman Adducts with Labile Acrylate Esters as Michael Acceptors by [3+2] Cycloaddition and Hoffmann-Type Elimination
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[25] Synthesis of isomeric 4-(N-methyltetrazolylamino)-2-phenyl-4H-thiopyrano[2,3-b]quinoline-3-carbaldehydes and 4-hydroxy-2-phenyl-4H-thiopyrano[2,3-b]quinoline-3-carbaldehyde based on tandem thiol-Michael and (aza)-Morita-Baylis-Hillman reactions and an in vitro study of the activity of the obtained compounds against influenza virus
Khramchikhin, Andrey V.
Skryl'nikova, Mariya A.
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Muryleva, Anna A.
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[26] DIASTEREOSELECTIVE SYNTHESIS OF TRANS-1,2-DISUBSTITUTED CYCLOPROPANOLS FROM HOMOALLYL OR BIS-HOMOALLYL ESTERS VIA TANDEM INTRAMOLECULAR NUCLEOPHILIC ACYL SUBSTITUTION AND INTRAMOLECULAR CARBONYL ADDITION-REACTIONS MEDIATED BY TI(OPR-I)(4)/2 I-PRMGBR REAGENT
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