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Catalytic asymmetric [3+2] cycloaddition of aromatic aldehydes with oxiranes by CC bond cleavage of epoxides: highly efficient synthesis of chiral 1,3-dioxolanes

A novel and efficient N,N -dioxideGd( iii ) complex was developed for the highly diastereo- and enantioselective [3+2] cycloaddition of aryl oxiranyl diketones and aldehydes via CC bond cleavage of oxiranes. The corresponding chiral 1,3-dioxolanes were obtained in excellent yields (up to 99%) with h... Full description

Journal Title: Chemical Communications 2014, Vol.50(17), pp.2161-2163
Main Author: Chen, Weiliang
Other Authors: Lin, Lili , Cai, Yunfei , Xia, Yong , Cao, Weidi , Liu, Xiaohua , Feng, Xiaoming
Format: Electronic Article Electronic Article
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ID: ISSN: 1359-7345 ; E-ISSN: 1364-548X ; DOI: 10.1039/c3cc48606k
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title: Catalytic asymmetric [3+2] cycloaddition of aromatic aldehydes with oxiranes by CC bond cleavage of epoxides: highly efficient synthesis of chiral 1,3-dioxolanes
format: Article
creator:
  • Chen, Weiliang
  • Lin, Lili
  • Cai, Yunfei
  • Xia, Yong
  • Cao, Weidi
  • Liu, Xiaohua
  • Feng, Xiaoming
subjects:
  • Aldehydes -- Chemistry
  • Dioxolanes -- Chemistry
  • Epoxy Compounds -- Chemistry
ispartof: Chemical Communications, 2014, Vol.50(17), pp.2161-2163
description: A novel and efficient N,N -dioxideGd( iii ) complex was developed for the highly diastereo- and enantioselective [3+2] cycloaddition of aryl oxiranyl diketones and aldehydes via CC bond cleavage of oxiranes. The corresponding chiral 1,3-dioxolanes were obtained in excellent yields (up to 99%) with high diastereoselectivities (>95:5 dr) and enantioselectivities (up to 91% ee). Moreover, a possible transition model was proposed to explain the origin of the asymmetric induction.
language:
source:
identifier: ISSN: 1359-7345 ; E-ISSN: 1364-548X ; DOI: 10.1039/c3cc48606k
fulltext: fulltext
issn:
  • 1359-7345
  • 1364-548X
  • 1364548X
  • 13597345
url: Link


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titleCatalytic asymmetric [3+2] cycloaddition of aromatic aldehydes with oxiranes by CC bond cleavage of epoxides: highly efficient synthesis of chiral 1,3-dioxolanes
creatorChen, Weiliang ; Lin, Lili ; Cai, Yunfei ; Xia, Yong ; Cao, Weidi ; Liu, Xiaohua ; Feng, Xiaoming
ispartofChemical Communications, 2014, Vol.50(17), pp.2161-2163
identifier
descriptionA novel and efficient N,N -dioxideGd( iii ) complex was developed for the highly diastereo- and enantioselective [3+2] cycloaddition of aryl oxiranyl diketones and aldehydes via CC bond cleavage of oxiranes. The corresponding chiral 1,3-dioxolanes were obtained in excellent yields (up to 99%) with high diastereoselectivities (>95:5 dr) and enantioselectivities (up to 91% ee). Moreover, a possible transition model was proposed to explain the origin of the asymmetric induction.
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subjectAldehydes -- Chemistry ; Dioxolanes -- Chemistry ; Epoxy Compounds -- Chemistry;
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titleCatalytic asymmetric [3+2] cycloaddition of aromatic aldehydes with oxiranes by CC bond cleavage of epoxides: highly efficient synthesis of chiral 1,3-dioxolanes
descriptionA novel and efficient N,N -dioxideGd( iii ) complex was developed for the highly diastereo- and enantioselective [3+2] cycloaddition of aryl oxiranyl diketones and aldehydes via CC bond cleavage of oxiranes. The corresponding chiral 1,3-dioxolanes were obtained in excellent yields (up to 99%) with high diastereoselectivities (>95:5 dr) and enantioselectivities (up to 91% ee). Moreover, a possible transition model was proposed to explain the origin of the asymmetric induction.
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titleCatalytic asymmetric [3+2] cycloaddition of aromatic aldehydes with oxiranes by CC bond cleavage of epoxides: highly efficient synthesis of chiral 1,3-dioxolanes
authorChen, Weiliang ; Lin, Lili ; Cai, Yunfei ; Xia, Yong ; Cao, Weidi ; Liu, Xiaohua ; Feng, Xiaoming
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atitleCatalytic asymmetric [3+2] cycloaddition of aromatic aldehydes with oxiranes by CC bond cleavage of epoxides: highly efficient synthesis of chiral 1,3-dioxolanes
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abstractA novel and efficient N,N -dioxideGd( iii ) complex was developed for the highly diastereo- and enantioselective [3+2] cycloaddition of aryl oxiranyl diketones and aldehydes via CC bond cleavage of oxiranes. The corresponding chiral 1,3-dioxolanes were obtained in excellent yields (up to 99%) with high diastereoselectivities (>95:5 dr) and enantioselectivities (up to 91% ee). Moreover, a possible transition model was proposed to explain the origin of the asymmetric induction.
doi10.1039/c3cc48606k
pages2161-2163
date2014-01-30