کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
1349902 980416 2005 9 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
Fluorous derivatives of (1R,2R)-diaminocyclohexane as chiral ligands for metal-catalyzed asymmetric reactions
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی معدنی
پیش نمایش صفحه اول مقاله
Fluorous derivatives of (1R,2R)-diaminocyclohexane as chiral ligands for metal-catalyzed asymmetric reactions
چکیده انگلیسی

Perfluoroalkyl-substituted, enantiopure diamines derived from (1R,2R)-diaminocyclohexane were conveniently prepared from readily available precursors. In situ generated metal complexes of these ligands were tested as chiral catalysts in three standard asymmetric reactions (cyclopropanation of styrene, hydrogen transfer reduction of acetophenone, and allylic alkylation of 1,3-diphenyl-2-propenyl acetate) affording enantioselectivities of up to 47% in the copper-catalyzed cyclopropanation of styrene.

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(1R,2R)-N,N′-Bis(1H,1H-perfluorooctyl)-cyclohexane-1,2-diamineC22H16F30N2Ee = 100%[α]D20=-27.1 (c 0.2, Et2O)Source of chirality: (1R,2R)-diaminocyclohexaneAbsolute configuration: (1R,2R)

(1R,2R)-N,N′-Bis(1H,1H,2H,2H-perfluorodecyl)-cyclohexane-1,2-diamineC26H20F34N2Ee = 100%[α]D20=-28.1 (c 0.2, CH3OH)Source of chirality: (1R,2R)-diaminocyclohexaneAbsolute configuration: (1R,2R)

(1R,2R)-N,N′-Bis(1H,1H,2H,2H,3H,3H-perfluoroundecyl)-cyclohexane-1,2-diamineC28H24F34N2Ee = 100%[α]D20=-29.5 (c 0.2, Et2O)Source of chirality: (1R,2R)-diaminocyclohexaneAbsolute configuration: (1R,2R)

(1R,2R)-N,N′-Bis(1H,1H,2H,2H-perfluorododecyl)-cyclohexane-1,2-diamineC30H28F34N2Ee = 100%[α]D20=-27.1 (c 0.2, CH3OH)Source of chirality: (1R,2R)-diaminocyclohexaneAbsolute configuration: (1R,2R)

ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Tetrahedron: Asymmetry - Volume 16, Issue 13, 4 July 2005, Pages 2319–2327
نویسندگان
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