Synthesis and properties of phospha[5]helicenes bearing an inner-rim phosphorus center

Synthesis and properties of phospha[5]helicenes bearing an inner-rim phosphorus center

New phospha[5]helicene derivatives featuring angular fusion of phosphole and carbohelicene moieties have been synthesized using 7-hydroxybenzo[b]phosphole oxide as a key intermediate, which can be regioselectively prepared through one-pot multicomponent coupling. The structural behavior of the prese...

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Main Authors: Md. Shafiqur Rahman, Yoshikai, Naohiko
Other Authors: School of Physical and Mathematical Sciences
Format: Article
Language:English
Published: 2020
Subjects:
Science::Chemistry
Chirality
Oxides
Online Access:https://hdl.handle.net/10356/143717
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Institution: Nanyang Technological University
Language: English
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spelling sg-ntu-dr.10356-1437172023-02-28T19:40:46Z Synthesis and properties of phospha[5]helicenes bearing an inner-rim phosphorus center Md. Shafiqur Rahman Yoshikai, Naohiko School of Physical and Mathematical Sciences Science::Chemistry Chirality Oxides New phospha[5]helicene derivatives featuring angular fusion of phosphole and carbohelicene moieties have been synthesized using 7-hydroxybenzo[b]phosphole oxide as a key intermediate, which can be regioselectively prepared through one-pot multicomponent coupling. The structural behavior of the present phospha[5]helicene oxide, sulfide, and gold complex in the solid and solution states, along with DFT calculations, demonstrated close correlation between the P-centered chirality and the helical chirality as well as facile helicity inversion and equilibrium between the diastereomers in solution. Ministry of Education (MOE) Nanyang Technological University Accepted version This work was supported by Nanyang Technological University and Singapore Ministry of Education (MOE2016-T2-2-043 and RG114/18). We thank Dr. Yongxin Li (Nanyang Technological University) for his assistance with the X-ray crystallographic analysis. 2020-09-18T06:25:21Z 2020-09-18T06:25:21Z 2019 Journal Article Md. Shafiqur Rahman, & Yoshikai, N. (2019). Synthesis and properties of phospha[5]helicenes bearing an inner-rim phosphorus center. Organic Letters, 21(9), 3232-3236. doi:10.1021/acs.orglett.9b00955 1523-7060 https://hdl.handle.net/10356/143717 10.1021/acs.orglett.9b00955 30990704 9 21 3232 3236 en Organic Letters This document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic Letters, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acs.orglett.9b00955 application/pdf
institution Nanyang Technological University
building NTU Library
continent Asia
country Singapore
Singapore
content_provider NTU Library
collection DR-NTU
language English
topic Science::Chemistry
Chirality
Oxides
spellingShingle Science::Chemistry
Chirality
Oxides
Md. Shafiqur Rahman
Yoshikai, Naohiko
Synthesis and properties of phospha[5]helicenes bearing an inner-rim phosphorus center
description New phospha[5]helicene derivatives featuring angular fusion of phosphole and carbohelicene moieties have been synthesized using 7-hydroxybenzo[b]phosphole oxide as a key intermediate, which can be regioselectively prepared through one-pot multicomponent coupling. The structural behavior of the present phospha[5]helicene oxide, sulfide, and gold complex in the solid and solution states, along with DFT calculations, demonstrated close correlation between the P-centered chirality and the helical chirality as well as facile helicity inversion and equilibrium between the diastereomers in solution.
author2 School of Physical and Mathematical Sciences
author_facet School of Physical and Mathematical Sciences
Md. Shafiqur Rahman
Yoshikai, Naohiko
format Article
author Md. Shafiqur Rahman
Yoshikai, Naohiko
author_sort Md. Shafiqur Rahman
title Synthesis and properties of phospha[5]helicenes bearing an inner-rim phosphorus center
title_short Synthesis and properties of phospha[5]helicenes bearing an inner-rim phosphorus center
title_full Synthesis and properties of phospha[5]helicenes bearing an inner-rim phosphorus center
title_fullStr Synthesis and properties of phospha[5]helicenes bearing an inner-rim phosphorus center
title_full_unstemmed Synthesis and properties of phospha[5]helicenes bearing an inner-rim phosphorus center
title_sort synthesis and properties of phospha[5]helicenes bearing an inner-rim phosphorus center
publishDate 2020
url https://hdl.handle.net/10356/143717
_version_ 1759856736032784384

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