Sigillin A, eine einzigartige polychlorierte Wehrsubstanz gegen Arthropoden aus dem Schneefloh <i>Ceratophysella sigillata</i>

Scheme 2. One-pot synthesis of trichloromethylated spiro-isoxazoline 6 from 1e. Scheme 3. Direct enantioselective allylic substitutionr eactions with RÀ Hcompounds using Me 3 SiCF 3 .A )(DHQD) 2 PHAL (20 mol %) in CH 2 Cl 2 (1.0 m); B) (DHQD) 2 PHAL (10 mol %) in CH 2 Cl 2 (0.5 m); C) (DHQD) 2 AQN (10 mol %) in CH 2 Cl 2 (0.5 m); D) (DHQD) 2 AQN (10 mol %) in CH 2 Cl 2 (0.5 m). Figure 1. Ap roposed reaction mechanism consistingo fthree important steps:i )C ÀFb ond activation, ii)c arbanion exchange of CF 3 to CCl 3 ,a nd iii)enantioselective SN 2 ' addition. Angewandte Chemie Communications 361 Te chnology (JST) Agency,a nd Kobayashi International Foundation.

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Enantioselective Trichloromethylation of MBH‐Fluorides with Chloroform Based on Silicon‐assisted C−F Activation and Carbanion Exchange Induced by a Ruppert–Prakash Reagent

Nishimine

Taira

Tokunaga

et al. 2015

Angewandte Chemie

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N‐Heterocyclic Carbene Catalyzed γ‐Dihalomethylenation of Enals by Single‐Electron Transfer

Yang

Dong

et al. 2016

Angewandte Chemie

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An N‐heterocyclic carbene (NHC) catalyzed dihalomethylenation of enals is described. It is a rare example of merging NHC catalysis with single‐electron chemistry, a challenging topic with limited previous success. The versatile carbon‐centered trihalomethyl radicals have been demonstrated, for the first time, to be compatible with an NHC‐bound intermediate, thus leading to efficient and regioselective intermolecular C−C bond formation. The mild process provides straightforward access to unsaturated δ,δ‐dihalo esters.

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Enantioselective Trichloromethylation of MBH‐Fluorides with Chloroform Based on Silicon‐assisted C−F Activation and Carbanion Exchange Induced by a Ruppert–Prakash Reagent

et al. 2015

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Enantioselective trichloromethylation of Morita-Baylis-Hillman (MBH)-type allylic fluorides with chloroform (HCCl3 ) under organocatalysis was achieved with high to excellent enantioselectivities. Silicon-assisted CF bond activation by a Ruppert-Prakash reagent and direct activation of HCCl3 by a carbanion exchange process with trifluoromethyl (CF3 ) carbanion generated in situ from the Ruppert-Prakash reagent realized the direct asymmetric trichloromethylation at a stereogenic allylic positon, without any help from transition metal catalysis, and under very mild conditions. Pre-activation of HCCl3 was not required. This method was extended to the direct enantioselective introduction of other C-H compounds such as alkyne, arene, indene, and FBSM without any pre-activation under a metal-free system.

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Sigillin A, eine einzigartige polychlorierte Wehrsubstanz gegen Arthropoden aus dem Schneefloh Ceratophysella sigillata

Cited by 6 publications

References 41 publications

Enantioselective Trichloromethylation of MBH‐Fluorides with Chloroform Based on Silicon‐assisted C−F Activation and Carbanion Exchange Induced by a Ruppert–Prakash Reagent

Enantioselective Trichloromethylation of MBH‐Fluorides with Chloroform Based on Silicon‐assisted C−F Activation and Carbanion Exchange Induced by a Ruppert–Prakash Reagent

N‐Heterocyclic Carbene Catalyzed γ‐Dihalomethylenation of Enals by Single‐Electron Transfer

Enantioselective Trichloromethylation of MBH‐Fluorides with Chloroform Based on Silicon‐assisted C−F Activation and Carbanion Exchange Induced by a Ruppert–Prakash Reagent

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