کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
---|---|---|---|---|
1349902 | 980416 | 2005 | 9 صفحه PDF | دانلود رایگان |
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)
Journal: Tetrahedron: Asymmetry - Volume 16, Issue 13, 4 July 2005, Pages 2319–2327