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Diindeno[7,1-de:1',7'-fg][1,3,2]dioxaphosphocin-5-amine,10,11,12,13-tetrahydro-N,N-dimethyl-, (11aS)- (9CI)

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CAS: 443965-10-4
MF: C19H20NO2P
MW: 325.3414
Synonyms: Diindeno[7,1-de:1',7'-fg][1,3,2]dioxaphosphocin-5-amine,10,11,12,13-tetrahydro-N,N-dimethyl-, (11aS)- (9CI)
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Qi-Lin Zhou

Nankai University
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Palladium-catalyzed asymmetric umpolung allylation of imines with allylic alcohols
Co-reporter: Xiang-Chen Qiao, Shou-Fei Zhu, Wang-Qiao Chen, Qi-Lin Zhou
pp: 1216-1220
Publication Date(Web):17 May 2010
DOI: 10.1016/j.tetasy.2010.03.003
A palladium-catalyzed asymmetric umpolung allylation reaction of imines with allylic alcohols has been developed. In the presence of chiral spiro phosphoramidite ligand 4, the allylation was accomplished with high yields and good enantioselectivities. The use of highly stable and easily available allylic alcohols instead of allylic metal reagents facilitated the preparation of chiral homoallylic amines.Image for unlabelled figureGraphical absImgN-(1-Phenylbut-3-enyl)-4-methylbenzenesulfonamideC17H19NO2SEe = 68%View the MathML source[α]D15=-60.6 (c 0.5, CH2Cl2)Source of chirality: asymmetric synthesisAbsolute configuration: unknownGraphical absImgN-(1-(4-Fluorophenyl)but-3-enyl)-4-methylbenzenesulfonamideC17H18FNO2SEe = 77%View the MathML source[α]D19=+55.2 (c 0.5, CH2Cl2)Source of chirality: asymmetric synthesisAbsolute configuration: unknownGraphical absImgN-(1-(4-Chlorophenyl)but-3-enyl)-4-methylbenzenesulfonamideC17H18ClNO2SEe = 80%View the MathML source[α]D18=-80.4 (c 0.5, CH2Cl2)Source of chirality: asymmetric synthesisAbsolute configuration: unknownGraphical absImgN-(1-(4-Trifluoromethylphenyl)but-3-enyl)-4-methylbenzenesulfonamideC18H18F3NO2SEe = 79%View the MathML source[α]D18=-58.6 (c 0.5, CH2Cl2)Source of chirality: asymmetric synthesisAbsolute configuration: unknownGraphical absImgN-(1-(4-Methylphenyl)but-3-enyl)-4-methylbenzenesulfonamideC18H21NO2SEe = 69%View the MathML source[α]D19=+66.4 (c 0.5, CH2Cl2)Source of chirality: asymmetric synthesisAbsolute configuration: unknownGraphical absImgN-(1-(4-Methoxyphenyl)but-3-enyl)-4-methylbenzenesulfonamideC18H21NO3SEe = 74%View the MathML source[α]D18=-69.6 (c 0.5, CH2Cl2)Source of chirality: asymmetric synthesisAbsolute configuration: unknownGraphical absImgN-(1-(3-Chlorophenyl)but-3-enyl)-4-methylbenzenesulfonamideC17H18ClNO2SEe = 58%View the MathML source[α]D18=-45.4 (c 1.8, CH2Cl2)Source of chirality: asymmetric synthesisAbsolute configuration: unknownGraphical absImgN-(1-m-Tolylbut-3-enyl)-4-methyl-benzenesulfonamideC18H21NO2SEe = 46%View the MathML source[α]D18=-36.5 (c 1.75, CH2Cl2)Source of chirality: asymmetric synthesisAbsolute configuration: unknownGraphical absImgN-(1-(2-Chlorophenyl)but-3-enyl)-4-methylbenzenesulfonamideC17H18ClNO2SEe = 65%View the MathML source[α]D18=-44.2 (c 0.5, CH2Cl2)Source of chirality: asymmetric synthesisAbsolute configuration: unknownGraphical absImgN-(1-(2-Methoxyphenyl)but-3-enyl)-4-methylbenzenesulfonamideC18H21NO3SEe = 64%View the MathML source[α]D18=-26.0 (c 1.6, CH2Cl2)Source of chirality: asymmetric synthesisAbsolute configuration: unknownGraphical absImg(S)-N-(1-(Furan-2-yl)but-3-enyl)-4-methylbenzenesulfonamideC15H17NO3SEe = 75%View the MathML source[α]D15=-43.6 (c 0.5, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (S)Graphical absImg(E)-4-Methyl-N-(1-phenylhexa-1,5-diene-3-yl)benzenesulfonamideC19H21NO2SEe = 76%View the MathML source[α]D18=-91.2 (c 1.2, CH2Cl2)Source of chirality: asymmetric synthesisAbsolute configuration: unknownGraphical absImgN-(1-Cyclohexylbut-3-enyl)-4-methylbenzenesulfonamideC17H25NO2SEe = 77%View the MathML source[α]D19=+8.8 (c 0.5, CH2Cl2)Source of chirality: asymmetric synthesisAbsolute configuration: unknownGraphical absImgN-(1-Phenylbut-3-enyl)-4-(trifluoromethyl)benzenesulfonamideC17H16F3NO2SEe = 60%View the MathML source[α]D15=+24.6 (c 0.98, CH2Cl2)Source of chirality: asymmetric synthesisAbsolute configuration: unknownGraphical absImgN-(1-Phenylbut-3-enyl)-4-methoxybenzenesulfonamideC17H19NO3SEe = 67%View the MathML source[α]D15=+44.5 (c 1.58, CH2Cl2)Source of chirality: asymmetric synthesisAbsolute configuration: unknownGraphical absImg(S)-N-(1-Phenylbut-3-enyl)benzenesulfonamideC16H17NO2SEe = 63%View the MathML source[α]D15=-43.4 (c 0.5, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (S)Graphical absImgsyn-N-(2-Methyl-1-phenylbut-3-enyl)-4-methylbenzenesulfonamideC18H21NO2SEe = 69%View the MathML source[α]D19=+55.4 (c 0.5, CH2Cl2)Source of chirality: asymmetric synthesisAbsolute configuration: unknownGraphical absImgsyn-N-(1,2-Diphenylbut-3-enyl)-4-methylbenzenesulfonamideC23H23NO2SEe = 65%View the MathML source[α]D19=+15.6 (c 0.5, CH2Cl2)Source of chirality: asymmetric synthesisAbsolute configuration: unknownGraphical absImgN-(3-Methyl-1-phenylbut-3-enyl)-4-methylbenzenesulfonamideC18H21NO2SEe = 81%View the MathML source[α]D19=+95 (c 0.5, CH2Cl2)Source of chirality: asymmetric synthesisAbsolute configuration: unknown