Applications of helical-chiral pyridines as organocatalysts in asymmetric synthesis

Zhili Peng; Norito Takenaka

doi:10.1002/tcr.201200010

Applications of helical-chiral pyridines as organocatalysts in asymmetric synthesis

Zhili Peng, Norito Takenaka

Chemistry

Research output: Contribution to journal › Article › peer-review

50 Scopus citations

Abstract

A new family of chiral pyridines has been designed and synthesized for use in asymmetric organocatalysis. Thus, helical-chiral pyridines induce high enantioselectivity in a range of mechanistically unrelated, synthetically significant transformations, including Friedel-Crafts alkylation with nitroalkenes, periselective Diels-Alder reactions with nitroalkenes, the ring-opening of epoxides with a chloride nucleophile, and the propargylation of aldehydes.

Original language	English (US)
Pages (from-to)	28-42
Number of pages	15
Journal	Chemical Record
Volume	13
Issue number	1
DOIs	https://doi.org/10.1002/tcr.201200010
State	Published - Feb 2013

Keywords

asymmetric catalysis
enantioselectivity
helical structures
organocatalysis
pyridines

ASJC Scopus subject areas

Chemistry(all)
Biochemistry
Chemical Engineering(all)
Materials Chemistry

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abstract = "A new family of chiral pyridines has been designed and synthesized for use in asymmetric organocatalysis. Thus, helical-chiral pyridines induce high enantioselectivity in a range of mechanistically unrelated, synthetically significant transformations, including Friedel-Crafts alkylation with nitroalkenes, periselective Diels-Alder reactions with nitroalkenes, the ring-opening of epoxides with a chloride nucleophile, and the propargylation of aldehydes.",

keywords = "asymmetric catalysis, enantioselectivity, helical structures, organocatalysis, pyridines",

author = "Zhili Peng and Norito Takenaka",

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AU - Takenaka, Norito

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N2 - A new family of chiral pyridines has been designed and synthesized for use in asymmetric organocatalysis. Thus, helical-chiral pyridines induce high enantioselectivity in a range of mechanistically unrelated, synthetically significant transformations, including Friedel-Crafts alkylation with nitroalkenes, periselective Diels-Alder reactions with nitroalkenes, the ring-opening of epoxides with a chloride nucleophile, and the propargylation of aldehydes.

AB - A new family of chiral pyridines has been designed and synthesized for use in asymmetric organocatalysis. Thus, helical-chiral pyridines induce high enantioselectivity in a range of mechanistically unrelated, synthetically significant transformations, including Friedel-Crafts alkylation with nitroalkenes, periselective Diels-Alder reactions with nitroalkenes, the ring-opening of epoxides with a chloride nucleophile, and the propargylation of aldehydes.

KW - asymmetric catalysis

KW - enantioselectivity

KW - helical structures

KW - organocatalysis

KW - pyridines

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Applications of helical-chiral pyridines as organocatalysts in asymmetric synthesis

Abstract

Keywords

ASJC Scopus subject areas

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