کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
1346681 1500366 2010 7 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
Organocatalytic Michael addition of aldehydes to a β-silylmethylene malonate to form intermediates for the enantioselective synthesis of hydroxylated valerolactones and piperidines
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی معدنی
پیش نمایش صفحه اول مقاله
Organocatalytic Michael addition of aldehydes to a β-silylmethylene malonate to form intermediates for the enantioselective synthesis of hydroxylated valerolactones and piperidines
چکیده انگلیسی

The direct Michael addition of enolizable aldehydes to dimethyl(phenyl)silylmethylene malonate was catalysed by an (S)-diphenylprolinol trimethylsilyl ether/acetic acid combination. The adducts were formed in good yield, high diastereoselectivity and excellent enantioselectivity. Chiral valerolactone and piperidine skeletons embedded with a silyl and other functionalities have been made out of the adducts. A total synthesis (+)-simplactone B has been achieved from one of the adducts.

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(4S,5S)-5-Ethyltetrahydro-4-dimethylphenylsilyl-2H-2-pyranoneC15H22O2SiEe = 97%[α]D26=+46.0 (c 1.34, CHCl3)Source of chirality: asymmetric induction and (S)-prolineAbsolute configuration: (4S,5S)

(4S,5S)-5-Ethyltetrahydro-4-hydroxy-2H-2-pyranoneC7H12O3[α]D25=+22.3 (c 0.94, CHCl3)Source of chirality: asymmetric induction and (S)-prolineAbsolute configuration: (4S,5S)

(3R,4S,5S)-5-Ethyltetrahydro-4-dimethylphenylsilyl-3-methyl-2H-2-pyranoneC16H24O2Si[α]D26=+37.2 (c 0.78, CHCl3)Source of chirality: asymmetric induction and (S)-prolineAbsolute configuration: (3R,4S,5S)

(3R,4S,5S)-1-Benzyl-4-dimethylphenylsilyl-5-ethyl-2-oxo-piperidine-3-carboxylic acid ethyl esterC25H33NO3Si[α]D27=-19.0 (c 1.0, CHCl3)Source of chirality: asymmetric induction and (S)-prolineAbsolute configuration: (3R,4S,5S)

(3R,4S,5S)-(1-Benzyl-4-dimethylphenylsilyl-5-ethyl-piperidine-3-yl)-methanolC23H33NOSi[α]D26=+5.0 (c 2.36, CHCl3).Source of chirality: asymmetric induction and (S)-prolineAbsolute configuration: (3R,4S,5S)

ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Tetrahedron: Asymmetry - Volume 21, Issues 21–22, 25 November 2010, Pages 2696–2702
نویسندگان
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