Ru(II)-Catalyzed Asymmetric Transfer Hydrogenation of Chalcones in Water: Application to the Enantioselective Synthesis of Flavans BW683C and Tephrowatsin E

The oxo-tethered-Ru(II) precatalyst promoted the one-pot CC/CO reduction of chalcones using sodium formate as the hydrogen source in water through asymmetric transfer hydrogenation. Twenty-seven 1,3-diarylpropan-1-ols were obtained in good to excellent yields (up to 96%) and enantiomeric purities...

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Veröffentlicht in:	Journal of organic chemistry 2022-11, Vol.87 (21), p.14208-14222
Hauptverfasser:	Demidoff, Felipe C., Caleffi, Guilherme S., Figueiredo, Marcella, Costa, Paulo R. R.
Format:	Artikel
Sprache:	eng
Schlagworte:	Catalysis Chalcone Chalcones Hydrogenation Polyphenols Stereoisomerism Water
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container_end_page	14222
container_issue	21
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container_title	Journal of organic chemistry
container_volume	87
creator	Demidoff, Felipe C. Caleffi, Guilherme S. Figueiredo, Marcella Costa, Paulo R. R.
description	The oxo-tethered-Ru(II) precatalyst promoted the one-pot CC/CO reduction of chalcones using sodium formate as the hydrogen source in water through asymmetric transfer hydrogenation. Twenty-seven 1,3-diarylpropan-1-ols were obtained in good to excellent yields (up to 96%) and enantiomeric purities (up to 98:2). Our data suggested that the enones are first reduced to the corresponding dihydrochalcones (1,4-selectivity) and then into 1,3-diarylpropan-1-ols (CO reduction). The stereoelectronic effects of electron-donating and electron-withdrawing groups at the ortho, meta and para positions of both aromatic rings were evaluated. The 2-OH group at the B ring was well tolerated, allowing a straightforward enantioselective synthesis of two flavans through the Mitsunobu cyclization, the antiviral (S)-BW683C and the natural flavan (S)-tephrowatsin E.
doi_str_mv	10.1021/acs.joc.2c01733
format	Article
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Chem</addtitle><date>2022-11-04</date><risdate>2022</risdate><volume>87</volume><issue>21</issue><spage>14208</spage><epage>14222</epage><pages>14208-14222</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><abstract>The oxo-tethered-Ru(II) precatalyst promoted the one-pot CC/CO reduction of chalcones using sodium formate as the hydrogen source in water through asymmetric transfer hydrogenation. Twenty-seven 1,3-diarylpropan-1-ols were obtained in good to excellent yields (up to 96%) and enantiomeric purities (up to 98:2). Our data suggested that the enones are first reduced to the corresponding dihydrochalcones (1,4-selectivity) and then into 1,3-diarylpropan-1-ols (CO reduction). The stereoelectronic effects of electron-donating and electron-withdrawing groups at the ortho, meta and para positions of both aromatic rings were evaluated. 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subjects	Catalysis Chalcone Chalcones Hydrogenation Polyphenols Stereoisomerism Water
title	Ru(II)-Catalyzed Asymmetric Transfer Hydrogenation of Chalcones in Water: Application to the Enantioselective Synthesis of Flavans BW683C and Tephrowatsin E
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