| Synthesis of Chiral β-Lactams by Pd-Catalyzed Enantioselective Amidation of Methylene C(sp3)-H Bonds |
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| 引用本文： | Tao Zhou,Meng-Xue Jiang,Xu Yang,Qiang Yue,Ye-Qiang Han,Yi Ding,Bing-Feng Shi. Synthesis of Chiral β-Lactams by Pd-Catalyzed Enantioselective Amidation of Methylene C(sp3)-H Bonds[J]. 中国化学, 2020, 38(3): 242-246. DOI: 10.1002/cjoc.201900533 |
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| 作者姓名： | Tao Zhou Meng-Xue Jiang Xu Yang Qiang Yue Ye-Qiang Han Yi Ding Bing-Feng Shi |
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| 作者单位： | Department of Chemistry;School of Biotechnology and Health Sciences;International Healthcare Innovation Institute（Jiangmen） |
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| 基金项目： | Financial support from the NSFC(Nos.21572201,21772170,21801223);the Chinese Postdoctoral Science Foundation(No.2017M621906);the Outstanding Young Talents of Zhejiang Prov-ince High-level Personnel of Special Support(ZJWR0108);the Fundamental Research Funds for the Central Universities(No.2018XZ2X001-02)is gratefully acknowledged. |
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| 摘 要： | A Pd(Ⅱ)-catalyzed enantioselective intramolecular amidation of both benzylic and unbiased methylene C(sp^3)-H bonds for the straightforward synthesis of chiral B-lactams from aliphatic carboxamides is reported.The combination of 2 prinylisopropyl(PIP)auxiiary with 3,3′-subtituted BINOL ligands is crucial for the enhancement of both reactivity and enantiocontrol of differentiating unbiased meth-ylene C(sp^3)-H bonds.The desired chemoselective C-N reductive elimination was achieved by employing 2-fluoro-1-iodo-4-nitrobenzene as oxidant.
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| 关 键 词： | bonds straight CHIRAL |
Synthesis of Chiral β‐Lactams by Pd‐Catalyzed Enantioselective Amidation of Methylene C(sp3)–H Bonds |
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| Tao Zhou,Meng‐Xue Jiang,Xu Yang,Qiang Yue,Ye‐Qiang Han,Yi Ding,Bing‐Feng Shi. Synthesis of Chiral β‐Lactams by Pd‐Catalyzed Enantioselective Amidation of Methylene C(sp3)–H Bonds[J]. Chinese Journal of Chemistry, 2020, 38(3): 242-246. DOI: 10.1002/cjoc.201900533 |
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| Authors: | Tao Zhou Meng‐Xue Jiang Xu Yang Qiang Yue Ye‐Qiang Han Yi Ding Bing‐Feng Shi |
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| Abstract: | A Pd(II)‐catalyzed enantioselective intramolecular amidation of both benzylic and unbiased methylene C(sp3)?H bonds for the straightforward synthesis of chiral β‐lactams from aliphatic carboxamides is reported. The combination of 2‐pyridinylisopropyl (PIP) auxiliary with 3,3’‐substituted BINOL ligands is crucial for the enhancement of both reactivity and enantiocontrol of differentiating unbiased methylene C(sp3)?H bonds. The desired chemoselective C—N reductive elimination was achieved by employing 2‐fluoro‐1‐iodo‐4‐nitrobenzene as oxidant. |
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