Catalytic asymmetric diarylphosphine addition to α-diazoesters for the synthesis of P-stereogenic phosphinates via P*-N bond formation

Catalytic asymmetric diarylphosphine addition to α-diazoesters for the synthesis of P-stereogenic phosphinates via P*-N bond formation

The asymmetric catalytic P-H addition of racemic secondary phosphines to electrophilic α-diazoesters via P*-N bond formation is disclosed for the first time. Interaction between the diazoester and the palladium catalyst resulted in the unusually enhanced electrophilic ability of the terminal nitroge...

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Main Authors: Balázs, László B., Huang, Yinhua, Khalikuzzaman, Jasmina B., Li, Yongxin, Pullarkat, Sumod A., Leung, Pak-Hing
Other Authors: School of Physical and Mathematical Sciences
Format: Article
Language:English
Published: 2022
Subjects:
Science::Chemistry
Alpha Diazoester Derivative
Diarylphosphine
Online Access:https://hdl.handle.net/10356/159533
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Institution: Nanyang Technological University
Language: English
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spelling sg-ntu-dr.10356-1595332022-06-24T06:17:24Z Catalytic asymmetric diarylphosphine addition to α-diazoesters for the synthesis of P-stereogenic phosphinates via P*-N bond formation Balázs, László B. Huang, Yinhua Khalikuzzaman, Jasmina B. Li, Yongxin Pullarkat, Sumod A. Leung, Pak-Hing School of Physical and Mathematical Sciences Science::Chemistry Alpha Diazoester Derivative Diarylphosphine The asymmetric catalytic P-H addition of racemic secondary phosphines to electrophilic α-diazoesters via P*-N bond formation is disclosed for the first time. Interaction between the diazoester and the palladium catalyst resulted in the unusually enhanced electrophilic ability of the terminal nitrogen in the diazo functionality, as opposed to the commonly expected formation of a metal carbene by nitrogen elimination. Further derivatization of the generated phosphinic hydrazones provided access to enantioenriched P-stereogenic diarylphosphinates via a simple transformation. Ministry of Education (MOE) Nanyang Technological University We thank Nanyang Technological University for supporting this research (Grants M4080454 (NTU) and 2017-T1-001- 175-02 (MOE)) and for a SINGA scholarship to L.B.B. 2022-06-24T06:17:23Z 2022-06-24T06:17:23Z 2020 Journal Article Balázs, L. B., Huang, Y., Khalikuzzaman, J. B., Li, Y., Pullarkat, S. A. & Leung, P. (2020). Catalytic asymmetric diarylphosphine addition to α-diazoesters for the synthesis of P-stereogenic phosphinates via P*-N bond formation. Journal of Organic Chemistry, 85, 14763-14771. https://dx.doi.org/10.1021/acs.joc.0c00181 0022-3263 https://hdl.handle.net/10356/159533 10.1021/acs.joc.0c00181 32216341 2-s2.0-85098174524 85 14763 14771 en M4080454 2017-T1-001- 175-02 Journal of Organic Chemistry © 2020 American Chemical Society. 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
Alpha Diazoester Derivative
Diarylphosphine
spellingShingle Science::Chemistry
Alpha Diazoester Derivative
Diarylphosphine
Balázs, László B.
Huang, Yinhua
Khalikuzzaman, Jasmina B.
Li, Yongxin
Pullarkat, Sumod A.
Leung, Pak-Hing
Catalytic asymmetric diarylphosphine addition to α-diazoesters for the synthesis of P-stereogenic phosphinates via P*-N bond formation
description The asymmetric catalytic P-H addition of racemic secondary phosphines to electrophilic α-diazoesters via P*-N bond formation is disclosed for the first time. Interaction between the diazoester and the palladium catalyst resulted in the unusually enhanced electrophilic ability of the terminal nitrogen in the diazo functionality, as opposed to the commonly expected formation of a metal carbene by nitrogen elimination. Further derivatization of the generated phosphinic hydrazones provided access to enantioenriched P-stereogenic diarylphosphinates via a simple transformation.
author2 School of Physical and Mathematical Sciences
author_facet School of Physical and Mathematical Sciences
Balázs, László B.
Huang, Yinhua
Khalikuzzaman, Jasmina B.
Li, Yongxin
Pullarkat, Sumod A.
Leung, Pak-Hing
format Article
author Balázs, László B.
Huang, Yinhua
Khalikuzzaman, Jasmina B.
Li, Yongxin
Pullarkat, Sumod A.
Leung, Pak-Hing
author_sort Balázs, László B.
title Catalytic asymmetric diarylphosphine addition to α-diazoesters for the synthesis of P-stereogenic phosphinates via P*-N bond formation
title_short Catalytic asymmetric diarylphosphine addition to α-diazoesters for the synthesis of P-stereogenic phosphinates via P*-N bond formation
title_full Catalytic asymmetric diarylphosphine addition to α-diazoesters for the synthesis of P-stereogenic phosphinates via P*-N bond formation
title_fullStr Catalytic asymmetric diarylphosphine addition to α-diazoesters for the synthesis of P-stereogenic phosphinates via P*-N bond formation
title_full_unstemmed Catalytic asymmetric diarylphosphine addition to α-diazoesters for the synthesis of P-stereogenic phosphinates via P*-N bond formation
title_sort catalytic asymmetric diarylphosphine addition to α-diazoesters for the synthesis of p-stereogenic phosphinates via p*-n bond formation
publishDate 2022
url https://hdl.handle.net/10356/159533
_version_ 1736856419363192832

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