Jump to main content
Jump to site search

Issue 37, 2019
Previous Article Next Article

Synthesis of helical π-conjugated polymers bearing pyridine N-oxide pendants and asymmetric allylation of aldehydes in the helical cavity

Author affiliations

Abstract

Catalytically active chiral π-conjugated polymers (poly-1(NO)r) bearing pyridine N-oxide pendants were synthesized by ternary copolymerization of a D-glucose-bound diethynyl compound with two types of thieno[3,4-b]thiophene comonomer, one of which contained a pyridine N-oxide group. When the pyridine N-oxide content in the copolymer was 10 mol% (poly-1(NO)0.10), the polymer backbone formed a one-handed helical structure in acetonitrile. Pyridine N-oxide pendants arranged inside the helical cavity of poly-1(NO)0.10 exhibited catalytic activity for the asymmetric allylation of benzaldehydes, producing the corresponding allyl alcohols with up to 43% ee.

Graphical abstract: Synthesis of helical π-conjugated polymers bearing pyridine N-oxide pendants and asymmetric allylation of aldehydes in the helical cavity

Back to tab navigation

Supplementary files

Article information


Submitted
19 Aug 2019
Accepted
07 Sep 2019
First published
09 Sep 2019

Org. Biomol. Chem., 2019,17, 8537-8540
Article type
Communication

Synthesis of helical π-conjugated polymers bearing pyridine N-oxide pendants and asymmetric allylation of aldehydes in the helical cavity

T. Ikai and T. Yoshida, Org. Biomol. Chem., 2019, 17, 8537
DOI: 10.1039/C9OB01828J

Social activity

Search articles by author

Spotlight

Advertisements