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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[2] Enantiopure Derivatives of Aza-Baylis-Hillman Adducts by Subsequent SN′-SN′ Reactions of Acylcarbamates Bearing a Chiral Auxiliary
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[3] Diastereoselective Baylis-Hillman reactions: The design and synthesis of a novel camphor-based chiral auxiliary
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[4] Selective [3+2] Huisgen Cycloaddition. Synthesis of Trans-Disubstituted Triazolodiazepines from Aza-Baylis-Hillman Adducts
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[5] Asymmetric Synthesis of 2-Alkyl-Substituted 2,5-Dihydropyrroles from Optically Active Aza-Baylis-Hillman Adducts. Formal Synthesis of (-)-Trachelanthamidine
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[6] Synthesis of Diastereoenriched α-Aminomethyl Enaminones via a Bronsted Acid-Catalyzed Asymmetric aza-Baylis-Hillman Reaction of Chiral N-Phosphonyl Imines
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[7] Regio- and Diastereoselective Synthesis of Dihydropyridopyrimidines via Cascade Reactions of 2-Aminopyridines with Morita-Baylis-Hillman Bromides of Nitroalkenes
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[8] Catalytic, asymmetric aza-Baylis-Hillman reaction of N-sulfonated imines with 2-cyclohexen-l-one and 2-cyclopenten-1-one in the presence of a chiral phosphine Lewis base
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TETRAHEDRON-ASYMMETRY, 2005, 16 (07) : 1385 - 1391
[9] Diastereoselective Synthesis of Substituted 2-Amino-1,3-propanediols from Morita-Baylis-Hillman Adducts
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[10] Diastereoselective Baylis-Hillman type reactions of chiral non-racemic N-sulfinimines with cyclopent-2-en-1-one
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