Enantioselective copper-catalyzed hydrophosphination of alkenyl isoquinolines

Yang, Qingjing; Zhou, Jian; Wang, Jun

doi:10.1039/d2sc06950d

Cited by 13 publications

(17 citation statements)

References 70 publications

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“…NMR Spectra were recorded on a Bruker DPX-500 (400) spectrometer at 500 MHz or 400 MHz for 1 H NMR, 160 MHz for 31 P NMR and 100 MHz or 125 MHz for 13 C NMR in CDCl3 with tetramethylsilane (TMS) or the residual deuterated solvent peaks as internal standard. Chemical shifts (δ) are reported in ppm, and coupling constants (J) are in Hertz (Hz).…”

Section: Synthesis Papermentioning

confidence: 99%

“…1-bromonaphthalen-2-yl 3-methylbenzoate (2d) 13 C NMR (100 MHz, CDCl3) δ 164. 7, 146.7, 138.6, 134.8, 132.8, 132.5, 131.0, 129.0, 128.9, 128.6, 128.3, 127.9, 127.7, 127.1, 126.4, 122.1, 115.3, 21.4.…”

Section: Synthesis Papermentioning

confidence: 99%

“…3, 146.6, 133.9, 133.5, 133.2, 132.8, 132.7, 131.9, 129.8, 129.3, 129.2, 129.0, 128.3, 128.2, 128.2, 128.2, 128.1, 126.7, 126.4, 126.2, 126.2, 125.9, 125.7, 125.4, 121.8 ). 13 C NMR (100 MHz, CDCl3) δ 176. 8, 146.7, 133.9, 133.6, 133.0, 132.8, 131.75, 129.1, 128.9, 128.3, 128.1, 128.0, 128.0, 126.5, 126.3, 126.2, 126.1, 125.9, 125.5, 125.2, 121.8, 38.6, 26.4 13 C NMR (100 MHz, CDCl3) δ 165.3, 1467, 144.0, 133.9, 133.5, 132.9, 132.7, 131.8, 129.8, 129.3, 129.0, 129.0, 128.3, 128.2, 128.2, 128.1, 126.6, 126.5, 126.4, 126.2, 126.2, 125.8, 125.7, 125.4, 122.0, 21.7 13 C NMR (100 MHz, CDCl3) δ 165.…”

Section: Synthesis Papermentioning

confidence: 99%

“…13 C NMR (100 MHz, CDCl3) δ 176. 8, 146.7, 133.9, 133.6, 133.0, 132.8, 131.75, 129.1, 128.9, 128.3, 128.1, 128.0, 128.0, 126.5, 126.3, 126.2, 126.1, 125.9, 125.5, 125.2, 121.8, 38.6, 26.4 13 C NMR (100 MHz, CDCl3) δ 165.3, 1467, 144.0, 133.9, 133.5, 132.9, 132.7, 131.8, 129.8, 129.3, 129.0, 129.0, 128.3, 128.2, 128.2, 128.1, 126.6, 126.5, 126.4, 126.2, 126.2, 125.8, 125.7, 125.4, 122.0, 21.7 13 C NMR (100 MHz, CDCl3) δ 165. 5, 146.7, 138.0, 133.9, 133.9, 133.6, 132.9, 132.7, 131.9, 130.3, 129.3, 129.2, 129.0, 128.4, 128.2, 128.2, 128.1, 128.1, 126.9, 126.7, 126.4, 126.2, 126.2, 125.9, 125.7, 125.4, 121.8, 21 7, 140.4, 134.0, 133.6, 133.1, 132.8, 132.2, 131.8, 131.4, 130.6, 129.3, 129.1, 128.7, 128.3, 128.3, 128.2, 128.1, 126.7, 126.5, 126.3, 126.0, 125.7, 125.5, 125.4, 122.1, 21 7.42 (m, 9H), 7.36 -7.31 (m, 2H), 7.18 -7.12 (m, 2H).…”

Section: Synthesis Papermentioning

confidence: 99%

“…5, 146.7, 138.0, 133.9, 133.9, 133.6, 132.9, 132.7, 131.9, 130.3, 129.3, 129.2, 129.0, 128.4, 128.2, 128.2, 128.1, 128.1, 126.9, 126.7, 126.4, 126.2, 126.2, 125.9, 125.7, 125.4, 121.8, 21 7, 140.4, 134.0, 133.6, 133.1, 132.8, 132.2, 131.8, 131.4, 130.6, 129.3, 129.1, 128.7, 128.3, 128.3, 128.2, 128.1, 126.7, 126.5, 126.3, 126.0, 125.7, 125.5, 125.4, 122.1, 21 7.42 (m, 9H), 7.36 -7.31 (m, 2H), 7.18 -7.12 (m, 2H). 13 C NMR (100 MHz, CDCl3) δ 164. 4, 146.5, 139.7, 133.9, 133.6, 132.8, 132.6, 131.9, 131.9, 131.1, 129.4, 129.2, 129.0, 128.6, 128.3, 128.2, 128.1, 126.7, 126.4, 126.3, 126.1, 125.9, 125.8, 125.3, 121.6.…”

Section: Synthesis Papermentioning

confidence: 99%

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Chiral 1, n‐bis(boronate) plays a crucial role in organic synthesis and medicinal chemistry. However, their catalytic and asymmetric synthesis has long posed a challenge in terms of operability and accessibility from readily available substrates. The recent discovery of the C═C bond formation through β‐C elimination of methylenecyclopropanes (MCP) has provided an exciting opportunity to enhance molecular complexity. In this study, the catalyzed asymmetric cascade hydroboration of MCP is developed. By employing different ligands, various homoallylic boronate intermediate are obtained through the hydroboration ring opening process. Subsequently, the cascade hydroboration with HBpin or B2pin2 resulted in the synthesis of enantioenriched chiral 1,3‐ and 1,4‐bis(boronates) in high yields, accompanied by excellent chemo‐ and enantioselectivities. The selective transformation of these two distinct C─B bonds also demonstrated their application potential in organic synthesis.

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Transition metal‐catalyzed hydrofunctionalization of methylenecyclopropanes (MCPs) has presented a considerable challenge due to the difficult manipulation of regioselectivity and complicated reaction patterns. Herein, we report a straightforward Pd‐catalyzed ring‐opening hydrophosphinylation reaction of MCPs via highly selective C−C bond cleavage. This method allows for rapid and efficient access to a wide range of chiral allylic phosphine oxides in good yields and high enantioselectivities. Additionally, density functional theory (DFT) calculations were performed to elucidate the reaction mechanism and the origin of enantioselectivity.

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Enantioselective copper-catalyzed hydrophosphination of alkenyl isoquinolines

Abstract: An enantioselective hydrophosphination of alkenyl isoquinolines is developed by using copper-chiral diphosphine ligand catalyst. It provides a direct and atom-efficient approach to prepare a variety of chiral phosphines with isoquinoline...

Cited by 13 publications

References 70 publications

Palladium/Azaphos-Catalyzed Asymmetric Suzuki–Miyaura Coupling

Palladium/Azaphos-Catalyzed Asymmetric Suzuki–Miyaura Coupling

Enantio‐ and Regioselective Cascade Hydroboration of Methylenecyclopropanes for Facile Access to Chiral 1,3‐ and 1,4‐Bis(boronates)

Palladium‐Catalyzed Enantio‐ and Regioselective Ring‐Opening Hydrophosphinylation of Methylenecyclopropanes

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