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Guanidine Organocatalyst for the Asymmetric Mannich-Type Reaction between alpha -Isothiocyanato Imide and Sulfonyl Imines

A highly efficient bisguanidine organocatalyst has been developed for the asymmetric Mannich-type reaction of alpha -isothiocyanato imide with N-Ts-protected imines (Ts=tosyl, see scheme). A series of aromatic, alpha , beta -unsaturated, heteroaromatic, and aliphatic imines can be converted into the... Full description

Journal Title: Chemistry: A European Journal February 2011, Vol.17(9), pp.2583-2586
Main Author: Chen, Xiaohong
Other Authors: Dong, Shunxi , Qiao, Zhen , Zhu, Yin , Xie, Mingsheng , Lin, Lili , Liu, Xiaohua , Feng, Xiaoming
Format: Electronic Article Electronic Article
Language: English
Subjects:
ID: ISSN: 0947-6539 ; E-ISSN: 1521-3765 ; DOI: 10.1002/chem.201002571
Link: http://search.proquest.com/docview/1800486869/?pq-origsite=primo
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title: Guanidine Organocatalyst for the Asymmetric Mannich-Type Reaction between alpha -Isothiocyanato Imide and Sulfonyl Imines
format: Article
creator:
  • Chen, Xiaohong
  • Dong, Shunxi
  • Qiao, Zhen
  • Zhu, Yin
  • Xie, Mingsheng
  • Lin, Lili
  • Liu, Xiaohua
  • Feng, Xiaoming
subjects:
  • Imides
  • Derivatives
  • Asymmetry
  • Aliphatic Compounds
  • Guanidines
  • Imines
  • Analysis (MD)
  • Chemical Analysis (Ep)
  • Chemical Analysis (Ed)
  • Chemical Analysis (EC)
ispartof: Chemistry: A European Journal, February 2011, Vol.17(9), pp.2583-2586
description: A highly efficient bisguanidine organocatalyst has been developed for the asymmetric Mannich-type reaction of alpha -isothiocyanato imide with N-Ts-protected imines (Ts=tosyl, see scheme). A series of aromatic, alpha , beta -unsaturated, heteroaromatic, and aliphatic imines can be converted into the desired alpha , beta -diamino acid derivatives in good to excellent yields with high diastereoselectivities (up to >95:5 d.r.) and excellent enantioselectivities (up to >99% ee) under mild conditions. The possible transition state of the reaction was also proposed.
language: eng
source:
identifier: ISSN: 0947-6539 ; E-ISSN: 1521-3765 ; DOI: 10.1002/chem.201002571
fulltext: fulltext
issn:
  • 09476539
  • 0947-6539
  • 15213765
  • 1521-3765
url: Link


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titleGuanidine Organocatalyst for the Asymmetric Mannich-Type Reaction between alpha -Isothiocyanato Imide and Sulfonyl Imines
creatorChen, Xiaohong ; Dong, Shunxi ; Qiao, Zhen ; Zhu, Yin ; Xie, Mingsheng ; Lin, Lili ; Liu, Xiaohua ; Feng, Xiaoming
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subjectImides ; Derivatives ; Asymmetry ; Aliphatic Compounds ; Guanidines ; Imines ; Analysis (MD) ; Chemical Analysis (Ep) ; Chemical Analysis (Ed) ; Chemical Analysis (EC)
descriptionA highly efficient bisguanidine organocatalyst has been developed for the asymmetric Mannich-type reaction of alpha -isothiocyanato imide with N-Ts-protected imines (Ts=tosyl, see scheme). A series of aromatic, alpha , beta -unsaturated, heteroaromatic, and aliphatic imines can be converted into the desired alpha , beta -diamino acid derivatives in good to excellent yields with high diastereoselectivities (up to >95:5 d.r.) and excellent enantioselectivities (up to >99% ee) under mild conditions. The possible transition state of the reaction was also proposed.
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titleGuanidine Organocatalyst for the Asymmetric Mannich-Type Reaction between alpha -Isothiocyanato Imide and Sulfonyl Imines
descriptionA highly efficient bisguanidine organocatalyst has been developed for the asymmetric Mannich-type reaction of alpha -isothiocyanato imide with N-Ts-protected imines (Ts=tosyl, see scheme). A series of aromatic, alpha , beta -unsaturated, heteroaromatic, and aliphatic imines can be converted into the desired alpha , beta -diamino acid derivatives in good to excellent yields with high diastereoselectivities (up to >95:5 d.r.) and excellent enantioselectivities (up to >99% ee) under mild conditions. The possible transition state of the reaction was also proposed.
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titleGuanidine Organocatalyst for the Asymmetric Mannich-Type Reaction between alpha -Isothiocyanato Imide and Sulfonyl Imines
authorChen, Xiaohong ; Dong, Shunxi ; Qiao, Zhen ; Zhu, Yin ; Xie, Mingsheng ; Lin, Lili ; Liu, Xiaohua ; Feng, Xiaoming
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abstractA highly efficient bisguanidine organocatalyst has been developed for the asymmetric Mannich-type reaction of alpha -isothiocyanato imide with N-Ts-protected imines (Ts=tosyl, see scheme). A series of aromatic, alpha , beta -unsaturated, heteroaromatic, and aliphatic imines can be converted into the desired alpha , beta -diamino acid derivatives in good to excellent yields with high diastereoselectivities (up to >95:5 d.r.) and excellent enantioselectivities (up to >99% ee) under mild conditions. The possible transition state of the reaction was also proposed.
doi10.1002/chem.201002571
urlhttp://search.proquest.com/docview/1800486869/
date2011-02-25