A Convenient and Practical Method for the Synthesis of Aromatic Nthiophosphoryl Imines

Xu, Xinyuan; Wang, Chungui; Zhang, Zhenghong; Zeng, Zebing; Ma, Xinpeng; Zhao, Guofeng; Tang, Chuchi

doi:10.2174/157017806778559446

Cited by 17 publications

(2 citation statements)

References 2 publications

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“…All of the solvent was dried according to the standard method and used after fresh distillation. N-(Thio)phosphoryl imines were prepared according to the literature method [6].…”

Section: General Methodsmentioning

confidence: 99%

Distinct chemoselectivity in the reaction of N-(thio)phosphoryl imines with diethylzinc

Wang

et al. 2007

Journal of Organometallic Chemistry

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“…All of the solvent was dried according to the standard method and used after fresh distillation. N-(Thio)phosphoryl imines were prepared according to the literature method [6].…”

Section: General Methodsmentioning

confidence: 99%

Distinct chemoselectivity in the reaction of N-(thio)phosphoryl imines with diethylzinc

Wang

et al. 2007

Journal of Organometallic Chemistry

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“…We set out to evaluate the soft Lewis acid/hard Brønsted base cooperative catalytic system [17] in the Mannich-type reaction of N-(9-fluorenylidene)-a-aminoacetonitrile (1) with N-thioDpp-ketimine 8 a, [18] which bears two sp 3 -hybridized carbon atoms directly attached to the imino carbon atom. On the basis of the particular efficiency of Cu I in the activation of the thioDpp group, [19] several bisphosphine ligands were screened with readily available [Cu(CH 3 CN) 4 ]PF 6 .…”

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confidence: 99%

Catalytic Asymmetric Mannich‐Type Reaction of N‐Alkylidene‐α‐Aminoacetonitrile with Ketimines

et al. 2015

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Optically active vicinal diamines are versatile chiral building blocks in organic synthesis. A soft Lewis acid/hard Brønsted base cooperative catalyst allows for an efficient stereoselective coupling of N-alkylidene-a-aminoacetonitrile and ketimines to access this class of compounds bearing consecutive tetra-and trisubstituted stereogenic centers. The strategic use of a soft Lewis basic thiophosphinoyl group for ketimines is the key to promoting the reaction, and aliphatic ketimines serve as suitable substrates with as little as 3 mol % catalyst loading. Scheme 1. Background for this work.(diphenylthiophosphinoyl)ketimines has been developed. Ketimines bearing sp 3 substituents on the imine carbonyl group were generally used with high diastereo-and enantioselectivity. The use of the soft Lewis basic ketimine was the key to promoting the reaction with a soft Lewis acid/hard Brønsted base cooperative catalyst.

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Direct Catalytic Asymmetric Vinylogous Mannich‐Type Reaction of γ‐Butenolides with Ketimines

et al. 2013

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Ein kooperativer Katalysator aus einer weichen Lewis‐Säure und einer „harten“ Brønsted‐Base katalysierte die Titelreaktion. Die N‐Thiophosphinoyl‐Gruppe der Ketimine war entscheidend zur Überwindung der hohen Aktivierungsbarriere durch die „Weich‐weich“‐Wechselwirkung von Schwefel und Kupfer. Mannich‐Addukte mit einem tetrasubstituierten Stereozentrum wurden mit ausgezeichneten Diastereo‐ und Enantioselektivitäten hergestellt. TANIAPHOS=Ferrocenyl‐Ligand.

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A Convenient and Practical Method for the Synthesis of Aromatic Nthiophosphoryl Imines

Abstract: Thermal condensation of acetals with different thiophosphoramides at 120-160 °C resulted in the formation of the corresponding N-thiophosphoryl imines in good to excellent yield (80-98%) with high purity (>95%, determined by 1 H NMR and elemental analyses).

Cited by 17 publications

References 2 publications

Distinct chemoselectivity in the reaction of N-(thio)phosphoryl imines with diethylzinc

Distinct chemoselectivity in the reaction of N-(thio)phosphoryl imines with diethylzinc

Catalytic Asymmetric Mannich‐Type Reaction of N‐Alkylidene‐α‐Aminoacetonitrile with Ketimines

Direct Catalytic Asymmetric Vinylogous Mannich‐Type Reaction of γ‐Butenolides with Ketimines

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