کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
1347392 980307 2008 12 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
Parallel kinetic resolution of tert-butyl (RS)-6-alkyl-cyclohex-1-ene-carboxylates for the asymmetric synthesis of 6-alkyl-substituted cishexacin derivatives
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی معدنی
پیش نمایش صفحه اول مقاله
Parallel kinetic resolution of tert-butyl (RS)-6-alkyl-cyclohex-1-ene-carboxylates for the asymmetric synthesis of 6-alkyl-substituted cishexacin derivatives
چکیده انگلیسی

Excellent levels of enantiorecognition are displayed by tert-butyl (RS)-6-n-alkyl-cyclohex-1-ene-carboxylates in mutual kinetic resolutions with lithium (RS)-N-benzyl-N-(α-methylbenzyl)amide. Therefore a 50:50 pseudoenantiomeric mixture of lithium (S)-N-benzyl-N-(α-methylbenzyl)amide and lithium (R)-N-3,4-dimethoxybenzyl-N-(α-methylbenzyl)amide allows their efficient parallel kinetic resolution, affording differentially protected 6-n-alkyl-cishexacin derivatives in high yield and >95% de. N-Debenzylation and ester hydrolysis give access to the corresponding homochiral 6-n-alkyl-substituted cishexacin derivatives.

Parallel kinetic resolution of tert-butyl (RS)-6-n-alkyl-cyclohex-1-ene-carboxylates with a pseudoenantiomeric mixture of homochiral lithium amides gives access to (1R,2S,6R)- and (1S,2R,6S)-6-methyl-cishexacin.Figure optionsDownload as PowerPoint slide

tert-Butyl (1R,2S,6R,αS)-2-[N-benzyl-N-(α-methylbenzyl)amino]-6-methyl-cyclohexane-carboxylateC27H37NO2[α]D23=-92.7 (c 1.0 in CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (1R,2S,6R,αS)

tert-Butyl (1R,2S,6R,αS)-2-[N-benzyl-N-(α-methylbenzyl)amino]-6-ethyl-cyclohexane-carboxylateC28H39NO2[α]D23=-64.7 (c 1.0 in CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (1R,2S,6R,αS)

tert-Butyl (1R,2S,6S,αS)-2-[N-benzyl-N-(α-methylbenzyl)amino]-6-benzyl-cyclohexane-carboxylateC33H41NO2[α]D23=-36.0 (c 1.0 in CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (1R,2S,6S,αS)

tert-Butyl (1S,2R,6S,αR)-2-[N-3′,4′-dimethoxybenzyl-N-(α-methylbenzyl)amino]-6-methyl-cyclohexane-carboxylateC29H41NO4[α]D23=+80.9 (c 1.0 in CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (1S,2R,6S,αR)

tert-Butyl (1S,2R,6S,αR)-2-[N-3′,4′-dimethoxybenzyl-N-(α-methylbenzyl)amino]-6-ethyl-cyclohexane-carboxylateC30H43NO4[α]D23=+65.6 (c 1.0 in CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (1S,2R,6S,αR)

tert-Butyl (1S,2R,6R,αR)-2-[N-3′,4′-dimethoxybenzyl-N-(α-methylbenzyl)amino]-6-benzyl-cyclohexane-carboxylateC35H45NO4[α]D23=+26.5 (c 1.0 in CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (1S,2R,6R,αR)

tert-Butyl (1S,2R,6S,αR)-2-[N-(α-methylbenzyl)amino]-6-methyl-cyclohexane-carboxylateC20H31NO2[α]D23=-47.7 (c 1.0 in CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (1S,2R,6S,αR)

tert-Butyl (1R,2S,6R)-2-amino-6-methyl-cyclohexane-carboxylateC12H23NO2[α]D23=-3.7 (c 1.0 in CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (1R,2S,6R)

(1R,2S,6R)-2-Amino-6-methyl-cyclohexane-carboxylic acid hydrochlorideC8H16ClNO2[α]D23=-2.0 (c 1.0 in 1 M aq HCl)Source of chirality: asymmetric synthesisAbsolute configuration: (1R,2S,6R)

ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Tetrahedron: Asymmetry - Volume 19, Issue 24, 12 December 2008, Pages 2870–2881
نویسندگان
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