کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
1347673 980320 2008 12 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
Asymmetric synthesis of tetrahydrolipstatin and valilactone
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی معدنی
پیش نمایش صفحه اول مقاله
Asymmetric synthesis of tetrahydrolipstatin and valilactone
چکیده انگلیسی

The highly diastereoselective aldol reaction between acyl complexes of the iron chiral auxiliary [(η5-C5H5)Fe(CO)(PPh3)] and β-hydroxy aldehydes (obtained via a Noyori asymmetric hydrogenation), followed by a tandem oxidative decomplexation–cyclisation process gives access to β-substituted and α,β-disubstituted β-lactones in high ee. This methodology has been employed in the asymmetric syntheses of tetrahydrolipstatin and valilactone.

Stereoselective aldol reaction of a homochiral iron octanoyl complex, followed by tandem oxidative decomplexation–cyclisation facilitated the asymmetric syntheses of tetrahydrolipstatin and valilactone.Figure optionsDownload as PowerPoint slide

(S)-Carbonyl(cyclopentadienyl)[(R)-3-hydroxy-4,4-dimethylpentanoyl](triphenylphosphino)ironC31H34FeO3P[α]D25=+82.4 (c 0.2 in CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (SFe,3R)

(R)-Carbonyl(cyclopentadienyl)[(2R,3S)-2-methyl-3-hydroxy-4,4-dimethylpentanoyl](triphenylphosphino)ironC32H36FeO3P[α]D25=-210 (c 0.5 in CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (RFe,2R,3S)

(R)-Carbonyl(cyclopentadienyl)[(2R,3R)-2-methyl-3-hydroxy-4,4-dimethylpentanoyl](triphenylphosphino)ironC32H36FeO3P[α]D20=-129 (c 0.25 in CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (RFe,2R,3R)

(R)-4-tert-Butyloxetan-2-oneC7H12O2[α]D25=-12.6 (c 0.7 in CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (R)

(3R,4S)-3-Methyl-4-tert-butyloxetan-2-oneC8H14O2[α]D25=+33.1 (c 0.3 in CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (3R,4S)

(3R,4R)-3-Methyl-4-tert-butyloxetan-2-oneC8H14O2[α]D25=+11.5 (c 0.7 in CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (3R,4R)

(R)-N-α-Methylbenzyl (R)-3-hydroxy-4,4-dimethylpentanamideC15H23NO2[α]D20=+94.6 (c 0.5 in CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (3R,R)

Methyl (S)-3-hydroxytetradecanoateC15H30O3[α]D20=+17.9 (c 1.3 in CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (S)

Methyl (S)-3-benzyloxytetradecanoateC22H36O3[α]D20=+6.85 (c 1.1 in CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (S)

(S)-3-Benzyloxytetradecan-1-olC21H36O2[α]D20=+32.3 (c 1.45 in CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (S)

(S)-3-BenzyloxytetradecanalC21H34O2[α]D20=+32.3 (c 1.45 in CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (S)

(S)-Carbonyl(cyclopentadienyl)octanoyl(triphenylphosphino)ironC32H36FeO2P[α]D20=+123.2 (c 1.0 in CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (S)

(3S,4S,2′S)-3-Hexyl-4-(2′-hydroxytridec-1′-yl)oxetan-2-oneC22H42O3[α]D20=-14.8 (c 0.7 in CH2Cl2)Source of chirality: asymmetric synthesisAbsolute configuration: (3S,4S,2′S)

(2S,2′S,3′S)-1-(3′-Hexyl-4′-oxooxetan-2′-yl)tridecan-2-yl (S)-N-formyl-leucinateC29H53NO5[α]D20=-31.8 (c 0.37 in CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (2S,2′S,3′S,2″S)

Methyl (S)-3-hydroxyoctanoateC9H18O3[α]D20=+22.5 (c 1.1 in CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (S)

Methyl (S)-3-benzyloxyoctanoateC16H24O3[α]D20=+7.11 (c 1.2 in CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (S)

(S)-3-BenzyloxyoctanalC15H22O2[α]D20=+14.1 (c 1.0 in CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (S)

(3S,4S,2′S)-3-Hexyl-4-(2′-benzyloxyhept-1′-yl)oxetan-2-oneC23H36O3[α]D20=-2.45 (c 1.0 in CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (3S,4S,2′S)

(3S,4S,2′S)-3-Hexyl-4-(2′-hydroxyhept-1′-yl)oxetan-2-oneC16H30O3[α]D20=-17.0 (c 1.0 in CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (3S,4S,2′S)

(2S,2′S,3′S)-1-(3′-Hexyl-4′-oxooxetan-2′-yl)heptan-2-yl (S)-N-formyl-valinateC22H39NO5[α]D20=-31.5 (c 0.5 in CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (2S,2′S,3′S,2″S)

ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Tetrahedron: Asymmetry - Volume 19, Issue 22, 17 November 2008, Pages 2620–2631
نویسندگان
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