Phosphine-Promoted [3 + 3] Annulations of Aziridines With Allenoates: Facile Entry Into Highly Functionalized Tetrahydropyridines
نویسندگان
چکیده
منابع مشابه
Facile construction of highly functionalized 2-pyrrolines via FeCl(3)-catalyzed reaction of aziridines with arylalkynes.
A series of highly functionalized 2-pyrrolines have been constructed by using a novel FeCl(3)-catalyzed reaction of aziridines with arylalkynes, in which an aryl-substituted alkenyl cation is involved.
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Phosphine catalyzed enantioselective [3+2] cyclizations on 4-substituted 2,6-diarylidenecyclohexanones and 2,4-diarylidene-bicyclo[3.1.0]hexan-3-ones take place with high diastereo- and enantioselectivity levels. The process affords spirocyclic compounds with excellent stereochemical control of up to five stereogenic centres.
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The triphenylphosphine-catalyzed formal [3 + 2] cycloaddition of allenoates and trifluoromethylketones was realized to give the corresponding dihydrofurans in good yields with excellent γ-regioselectivities. Hydrogenation of the dihydrofurans gave 2,4,4-trisubstituted tetrahydrofurans in good yields with exclusive cis-selectivities.
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From our investigations on phosphine-catalyzed [4+2] annulations between α-alkyl allenoates and activated olefins for the synthesis of cyclohexenes, we discovered a hexamethylphosphorous triamide (HMPT)-catalyzed [4+2] reaction between α-alkyl allenoates 1 and arylidene malonates or arylidene cyanoacetates 2 that provides highly functionalized cyclohexenes 3 and 4 in synthetically useful yields...
متن کاملPhosphine-catalyzed dearomatizing [3+2] annulations of isoquinolinium methylides with allenes.
A phosphine-catalyzed dearomatizing [3+2] annulation of isoquinolinium methylides with allenoates or allenones yields highly functionalized pyrroloisoquinolines with high regioselectivity and in viable yields.
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ژورنال
عنوان ژورنال: Journal of the American Chemical Society
سال: 2009
ISSN: 0002-7863,1520-5126
DOI: 10.1021/ja8097349