Catalytic access to ferrocenyl phosphines bearing both planar and central chirality – A kinetic resolution approach via catalytic asymmetric P(III)–C bond formation

Catalytic access to ferrocenyl phosphines bearing both planar and central chirality – A kinetic resolution approach via catalytic asymmetric P(III)–C bond formation

A series of enantioenriched ferrocenyl monophosphines imbued with both central and planar chirality were obtained catalytically (80–99% ee) via the kinetic resolution of 1,2-disubstituted planar chiral ferrocenyl enone racemates. The synthetic approach utilized a chiral palladacycle to facilitate th...

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Main Authors: Abdul Sadeer, Kojima, Tadayuki, Ng, Jia Sheng, Gan, Kennard Jun Hao, Chew, Renta Jonathan, Li, Yongxin, Pullarkat, Sumod Appukuttan
Other Authors: School of Physical and Mathematical Sciences
Format: Article
Language:English
Published: 2021
Subjects:
Science::Chemistry
Asymmetric
Hydrophosphination
Online Access:https://hdl.handle.net/10356/154139
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Institution: Nanyang Technological University
Language: English
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spelling sg-ntu-dr.10356-1541392021-12-15T00:55:20Z Catalytic access to ferrocenyl phosphines bearing both planar and central chirality – A kinetic resolution approach via catalytic asymmetric P(III)–C bond formation Abdul Sadeer Kojima, Tadayuki Ng, Jia Sheng Gan, Kennard Jun Hao Chew, Renta Jonathan Li, Yongxin Pullarkat, Sumod Appukuttan School of Physical and Mathematical Sciences Division of Chemistry and Biological Chemistry Science::Chemistry Asymmetric Hydrophosphination A series of enantioenriched ferrocenyl monophosphines imbued with both central and planar chirality were obtained catalytically (80–99% ee) via the kinetic resolution of 1,2-disubstituted planar chiral ferrocenyl enone racemates. The synthetic approach utilized a chiral palladacycle to facilitate the asymmetric hydrophosphination (AHP) as a means to achieve high stereoselectivity. The enantioenriched ferrocenylphosphine products could be protected and further recrystallized to obtain ees up to 99%. The modularity of the phosphine framework obtained was demonstrated via derivatization of its functional handles via a simple nucleophilic substitution to yield optically pure bisphosphines. Ministry of Education (MOE) This research project is supported by Ministry of Education, Singapore under its AcRF Tier I grant 2017-T1-001-175-02. 2021-12-15T00:55:20Z 2021-12-15T00:55:20Z 2020 Journal Article Abdul Sadeer, Kojima, T., Ng, J. S., Gan, K. J. H., Chew, R. J., Li, Y. & Pullarkat, S. A. (2020). Catalytic access to ferrocenyl phosphines bearing both planar and central chirality – A kinetic resolution approach via catalytic asymmetric P(III)–C bond formation. Tetrahedron, 76(25), 131259-. https://dx.doi.org/10.1016/j.tet.2020.131259 0040-4020 https://hdl.handle.net/10356/154139 10.1016/j.tet.2020.131259 2-s2.0-85084994644 25 76 131259 en 2017-T1-001-175-02 Tetrahedron © 2020 Elsevier Ltd. All rights reserved.
institution Nanyang Technological University
building NTU Library
continent Asia
country Singapore
Singapore
content_provider NTU Library
collection DR-NTU
language English
topic Science::Chemistry
Asymmetric
Hydrophosphination
spellingShingle Science::Chemistry
Asymmetric
Hydrophosphination
Abdul Sadeer
Kojima, Tadayuki
Ng, Jia Sheng
Gan, Kennard Jun Hao
Chew, Renta Jonathan
Li, Yongxin
Pullarkat, Sumod Appukuttan
Catalytic access to ferrocenyl phosphines bearing both planar and central chirality – A kinetic resolution approach via catalytic asymmetric P(III)–C bond formation
description A series of enantioenriched ferrocenyl monophosphines imbued with both central and planar chirality were obtained catalytically (80–99% ee) via the kinetic resolution of 1,2-disubstituted planar chiral ferrocenyl enone racemates. The synthetic approach utilized a chiral palladacycle to facilitate the asymmetric hydrophosphination (AHP) as a means to achieve high stereoselectivity. The enantioenriched ferrocenylphosphine products could be protected and further recrystallized to obtain ees up to 99%. The modularity of the phosphine framework obtained was demonstrated via derivatization of its functional handles via a simple nucleophilic substitution to yield optically pure bisphosphines.
author2 School of Physical and Mathematical Sciences
author_facet School of Physical and Mathematical Sciences
Abdul Sadeer
Kojima, Tadayuki
Ng, Jia Sheng
Gan, Kennard Jun Hao
Chew, Renta Jonathan
Li, Yongxin
Pullarkat, Sumod Appukuttan
format Article
author Abdul Sadeer
Kojima, Tadayuki
Ng, Jia Sheng
Gan, Kennard Jun Hao
Chew, Renta Jonathan
Li, Yongxin
Pullarkat, Sumod Appukuttan
author_sort Abdul Sadeer
title Catalytic access to ferrocenyl phosphines bearing both planar and central chirality – A kinetic resolution approach via catalytic asymmetric P(III)–C bond formation
title_short Catalytic access to ferrocenyl phosphines bearing both planar and central chirality – A kinetic resolution approach via catalytic asymmetric P(III)–C bond formation
title_full Catalytic access to ferrocenyl phosphines bearing both planar and central chirality – A kinetic resolution approach via catalytic asymmetric P(III)–C bond formation
title_fullStr Catalytic access to ferrocenyl phosphines bearing both planar and central chirality – A kinetic resolution approach via catalytic asymmetric P(III)–C bond formation
title_full_unstemmed Catalytic access to ferrocenyl phosphines bearing both planar and central chirality – A kinetic resolution approach via catalytic asymmetric P(III)–C bond formation
title_sort catalytic access to ferrocenyl phosphines bearing both planar and central chirality – a kinetic resolution approach via catalytic asymmetric p(iii)–c bond formation
publishDate 2021
url https://hdl.handle.net/10356/154139
_version_ 1720447098211532800

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