Issue 37, 2019

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

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

Supplementary files

Article information

Article type
Communication
Submitted
19 ဩ 2019
Accepted
07 စက် 2019
First published
09 စက် 2019

Org. Biomol. Chem., 2019,17, 8537-8540

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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements