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

52 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

Access to Document

10.1002/tcr.201200010

Cite this

@article{8e4eff2af3ac4adfb75265d0ae67ee10,

title = "Applications of helical-chiral pyridines as organocatalysts in asymmetric synthesis",

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",

year = "2013",

month = feb,

doi = "10.1002/tcr.201200010",

language = "English (US)",

volume = "13",

pages = "28--42",

journal = "Chemical Record",

issn = "1527-8999",

publisher = "John Wiley and Sons Inc.",

number = "1",

}

TY - JOUR

T1 - Applications of helical-chiral pyridines as organocatalysts in asymmetric synthesis

AU - Peng, Zhili

AU - Takenaka, Norito

PY - 2013/2

Y1 - 2013/2

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

UR - http://www.scopus.com/inward/record.url?scp=84874227963&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84874227963&partnerID=8YFLogxK

U2 - 10.1002/tcr.201200010

DO - 10.1002/tcr.201200010

M3 - Article

C2 - 23172849

AN - SCOPUS:84874227963

VL - 13

SP - 28

EP - 42

JO - Chemical Record

JF - Chemical Record

SN - 1527-8999

IS - 1

ER -

Applications of helical-chiral pyridines as organocatalysts in asymmetric synthesis

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this