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P-Stereogenic β-Aminophosphines: Preparation and Applications in Enantioselective Organocatalysis.

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Title: P-Stereogenic β-Aminophosphines: Preparation and Applications in Enantioselective Organocatalysis.
Authors: Hsin Y. Su1, Taylor, Mark S.1 mtaylor@chem.utoronto.ca
Source: Journal of Organic Chemistry. 3/17/2017, Vol. 82 Issue 6, p3173-3182. 10p.
Abstract: The synthesis of stereodefined β-aminophosphines having both carbon- and phosphorus-based chirality centers is described. The method involves resolution of a mixture of β-aminophosphine oxide diastereomers accessed by ring-opening of an amino alcohol-derived cyclic sulfamidate. A stereospecific, borane-promoted reduction of β-aminophosphine oxides, which occurs under mild conditions and with inversion of configuration at phosphorus, is a key step in this process. The products obtained are new building blocks for the synthesis of P-chiral ligands and organocatalysts. In a proof-of-concept application in organocatalysis, the diastereomeric P-chiral β-aminophosphine-based bifunctional thioureas displayed significantly different activities in the Morita-Baylis-Hillman reaction of methyl acrylate with benzaldehyde derivatives. [ABSTRACT FROM AUTHOR]
Copyright of Journal of Organic Chemistry is the property of American Chemical Society and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract. (Copyright applies to all Abstracts.)
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  Data: P-Stereogenic β-Aminophosphines: Preparation and Applications in Enantioselective Organocatalysis.
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  Data: <searchLink fieldCode="AR" term="%22Hsin+Y%2E+Su%22">Hsin Y. Su</searchLink><relatesTo>1</relatesTo><br /><searchLink fieldCode="AR" term="%22Taylor%2C+Mark+S%2E%22">Taylor, Mark S.</searchLink><relatesTo>1</relatesTo><i> mtaylor@chem.utoronto.ca</i>
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  Data: <searchLink fieldCode="JN" term="%22Journal+of+Organic+Chemistry%22">Journal of Organic Chemistry</searchLink>. 3/17/2017, Vol. 82 Issue 6, p3173-3182. 10p.
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  Data: The synthesis of stereodefined β-aminophosphines having both carbon- and phosphorus-based chirality centers is described. The method involves resolution of a mixture of β-aminophosphine oxide diastereomers accessed by ring-opening of an amino alcohol-derived cyclic sulfamidate. A stereospecific, borane-promoted reduction of β-aminophosphine oxides, which occurs under mild conditions and with inversion of configuration at phosphorus, is a key step in this process. The products obtained are new building blocks for the synthesis of P-chiral ligands and organocatalysts. In a proof-of-concept application in organocatalysis, the diastereomeric P-chiral β-aminophosphine-based bifunctional thioureas displayed significantly different activities in the Morita-Baylis-Hillman reaction of methyl acrylate with benzaldehyde derivatives. [ABSTRACT FROM AUTHOR]
– Name: AbstractSuppliedCopyright
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  Data: <i>Copyright of Journal of Organic Chemistry is the property of American Chemical Society and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract.</i> (Copyright applies to all Abstracts.)
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        Value: 10.1021/acs.joc.7b00199
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              Text: 3/17/2017
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