Chiral N,N′‑Dioxide Ligands Tune Diastereoselectivity in Mg(II)-Catalyzed Asymmetric Ring-Opening Desymmetrization of Azetidiniums
A diastereodivergent asymmetric desymmetrization of azetidinium salts with benzothiazoleamides as carbon nucleophiles through a chiral N,N′-dioxide/Mg(II) complex-promoted ring-opening reaction is realized by tuning ligands. Both syn- and anti-chiral δ-amino acid derivatives bearing benzothiazole s...
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| Veröffentlicht in: | Organic letters 2023-10, Vol.25 (42), p.7612-7616 |
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| container_title | Organic letters |
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| creator | Li, Zhaojing Wang, Yan Liu, Deyang Ning, Lichao Pu, Maoping Lin, Lili Feng, Xiaoming |
| description | A diastereodivergent asymmetric desymmetrization of azetidinium salts with benzothiazoleamides as carbon nucleophiles through a chiral N,N′-dioxide/Mg(II) complex-promoted ring-opening reaction is realized by tuning ligands. Both syn- and anti-chiral δ-amino acid derivatives bearing benzothiazole structure were obtained in moderate to good yields and dr and ee values. DFT calculations indicated that the diastereodivergency stems from the different size of the chiral pocket formed by variable substructures of the ligands, leading to the opposite attack direction of the nucleophiles. |
| doi_str_mv | 10.1021/acs.orglett.3c02728 |
| format | Article |
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Both syn- and anti-chiral δ-amino acid derivatives bearing benzothiazole structure were obtained in moderate to good yields and dr and ee values. 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Lett</addtitle><date>2023-10-27</date><risdate>2023</risdate><volume>25</volume><issue>42</issue><spage>7612</spage><epage>7616</epage><pages>7612-7616</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>A diastereodivergent asymmetric desymmetrization of azetidinium salts with benzothiazoleamides as carbon nucleophiles through a chiral N,N′-dioxide/Mg(II) complex-promoted ring-opening reaction is realized by tuning ligands. Both syn- and anti-chiral δ-amino acid derivatives bearing benzothiazole structure were obtained in moderate to good yields and dr and ee values. 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| title | Chiral N,N′‑Dioxide Ligands Tune Diastereoselectivity in Mg(II)-Catalyzed Asymmetric Ring-Opening Desymmetrization of Azetidiniums |
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