Pd-catalyzed enantiodivergent and regiospecific phospha-michael addition of diphenylphosphine to 4-oxo-enamides : efficient access to chiral phosphinocarboxamides and their analogues

Pd-catalyzed enantiodivergent and regiospecific phospha-michael addition of diphenylphosphine to 4-oxo-enamides : efficient access to chiral phosphinocarboxamides and their analogues

The palladacycle-catalyzed asymmetric P-H addition of 4-oxo-enamides has been developed, which provides efficient access to phosphinocarboxamides and their analogues. Solvent-mediated reversal of stereoselectivity (ee from +96 % to −92 %) was observed, and the underlying mechanism that allows facile...

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Main Authors: Chew, Renta Jonathan, Li, Xi-Rui, Li, Yongxin, Pullarkat, Appukuttan Sumod, Leung, Pak-Hing
Other Authors: School of Physical and Mathematical Sciences
Format: Article
Language:English
Published: 2015
Subjects:
DRNTU::Science::Chemistry
Online Access:https://hdl.handle.net/10356/106877
http://hdl.handle.net/10220/25190
http://dx.doi.org/10.1002/chem.201406298
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Institution: Nanyang Technological University
Language: English
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spelling sg-ntu-dr.10356-1068772019-12-06T22:20:11Z Pd-catalyzed enantiodivergent and regiospecific phospha-michael addition of diphenylphosphine to 4-oxo-enamides : efficient access to chiral phosphinocarboxamides and their analogues Chew, Renta Jonathan Li, Xi-Rui Li, Yongxin Pullarkat, Appukuttan Sumod Leung, Pak-Hing School of Physical and Mathematical Sciences DRNTU::Science::Chemistry The palladacycle-catalyzed asymmetric P-H addition of 4-oxo-enamides has been developed, which provides efficient access to phosphinocarboxamides and their analogues. Solvent-mediated reversal of stereoselectivity (ee from +96 % to −92 %) was observed, and the underlying mechanism that allows facile access to both enantiomers of the product by judicious choice of solvents is revealed. 2015-03-09T03:12:16Z 2019-12-06T22:20:11Z 2015-03-09T03:12:16Z 2019-12-06T22:20:11Z 2015 2015 Journal Article Chew, R. J., Li, X.-R., Li, Y., Pullarkat, S. A., & Leung, P.-H. (2015). Pd-catalyzed enantiodivergent and regiospecific phospha-michael addition of diphenylphosphine to 4-oxo-enamides : efficient access to chiral phosphinocarboxamides and their analogues. Chemistry - A European journal, 21(12), 4800-4804 . 0947-6539 https://hdl.handle.net/10356/106877 http://hdl.handle.net/10220/25190 http://dx.doi.org/10.1002/chem.201406298 en Chemistry - A European journal © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
institution Nanyang Technological University
building NTU Library
country Singapore
collection DR-NTU
language English
topic DRNTU::Science::Chemistry
spellingShingle DRNTU::Science::Chemistry
Chew, Renta Jonathan
Li, Xi-Rui
Li, Yongxin
Pullarkat, Appukuttan Sumod
Leung, Pak-Hing
Pd-catalyzed enantiodivergent and regiospecific phospha-michael addition of diphenylphosphine to 4-oxo-enamides : efficient access to chiral phosphinocarboxamides and their analogues
description The palladacycle-catalyzed asymmetric P-H addition of 4-oxo-enamides has been developed, which provides efficient access to phosphinocarboxamides and their analogues. Solvent-mediated reversal of stereoselectivity (ee from +96 % to −92 %) was observed, and the underlying mechanism that allows facile access to both enantiomers of the product by judicious choice of solvents is revealed.
author2 School of Physical and Mathematical Sciences
author_facet School of Physical and Mathematical Sciences
Chew, Renta Jonathan
Li, Xi-Rui
Li, Yongxin
Pullarkat, Appukuttan Sumod
Leung, Pak-Hing
format Article
author Chew, Renta Jonathan
Li, Xi-Rui
Li, Yongxin
Pullarkat, Appukuttan Sumod
Leung, Pak-Hing
author_sort Chew, Renta Jonathan
title Pd-catalyzed enantiodivergent and regiospecific phospha-michael addition of diphenylphosphine to 4-oxo-enamides : efficient access to chiral phosphinocarboxamides and their analogues
title_short Pd-catalyzed enantiodivergent and regiospecific phospha-michael addition of diphenylphosphine to 4-oxo-enamides : efficient access to chiral phosphinocarboxamides and their analogues
title_full Pd-catalyzed enantiodivergent and regiospecific phospha-michael addition of diphenylphosphine to 4-oxo-enamides : efficient access to chiral phosphinocarboxamides and their analogues
title_fullStr Pd-catalyzed enantiodivergent and regiospecific phospha-michael addition of diphenylphosphine to 4-oxo-enamides : efficient access to chiral phosphinocarboxamides and their analogues
title_full_unstemmed Pd-catalyzed enantiodivergent and regiospecific phospha-michael addition of diphenylphosphine to 4-oxo-enamides : efficient access to chiral phosphinocarboxamides and their analogues
title_sort pd-catalyzed enantiodivergent and regiospecific phospha-michael addition of diphenylphosphine to 4-oxo-enamides : efficient access to chiral phosphinocarboxamides and their analogues
publishDate 2015
url https://hdl.handle.net/10356/106877
http://hdl.handle.net/10220/25190
http://dx.doi.org/10.1002/chem.201406298
_version_ 1681045897407889408

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