Abstract:
A comparison of the diastereomeric composition of Kabachnik–Fields reaction products with those of two reactions simulating its stereo-controlling steps showed that only the ‘imine’ mechanism works in the (MeO)2P(O)H–PhCHO-[(S),(R,S)-H2NCH(Ph)Me] system, like in the phosphite–imine system; in a similar system containing (R,S)-sec-butylamine, additional ‘nucleophilic amination’ of the initially formed α-hydroxybenzyl phosphonate occurs.
Document Type:
Article
Language: English
Citation:
M. N. Dimukhametov, E. V. Bayandina, E. Yu. Davydova, A. T. Gubaidullin, V. A. Alfonsov, “A stereochemical approach to the Kabachnik–Fields reaction mechanism”, Mendeleev Commun., 13:3 (2003), 150–151
Linking options:
https://www.mathnet.ru/eng/mendc3998
https://www.mathnet.ru/eng/mendc/v13/i3/p150
This publication is cited in the following 10 articles:
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Tayebeh Piri, Reza Peymanfar, Shahrzad Javanshir, Sara Amirnejat, “Magnetic BaFe12O19/Al2O3: An Efficient Heterogeneous Lewis Acid Catalyst for the Synthesis of α-Aminophosphonates (Kabachnik–Fields Reaction)”, Catal Lett, 149:12 (2019), 3384
Dominik Koszelewski, Ryszard Ostaszewski, “Biocatalytic Promiscuity of Lipases in Carbon‐Phosphorus Bond Formation”, ChemCatChem, 11:10 (2019), 2554
Tomasz Cytlak, Monika Skibińska, Patrycja Kaczmarek, Marcin Kaźmierczak, Magdalena Rapp, Maciej Kubicki, Henryk Koroniak, “Functionalization of α-hydroxyphosphonates as a convenient route toN-tosyl-α-aminophosphonates”, RSC Adv., 8:22 (2018), 11957
Neven A. Ganoub, Eman Sabry, Wafaa M. Abdou, “Overview on the phosphonation of the C=X functional groups utilizing alkyl phosphites”, Synthetic Communications, 47:18 (2017), 1631
Wafaa M. Abdou, Reham F. Barghash, Mohamed S. Bekheit, “Investigations of the Chemistry of Alkyl Phosphites Toward Nitrogen-Containing Compounds: Efficient Approaches to α-Amino-, β-Amino-, and/or Enaminophosphonates”, Synthetic Communications, 45:17 (2015), 1929
Dorota G. Piotrowska, Iwona E. Głowacka, Andrzej E. Wróblewski, “Stereochemistry of the Three-Component Reaction Between the Ley′S Aldehyde, Benzyl Amines, and Trialkyl Phosphites. A New Approach to the Protected Enantiomerically Pure 1-Amino-2,3-Dihydroxypropylphosphonates”, Phosphorus, Sulfur, and Silicon and the Related Elements, 189:7-8 (2014), 1237
Comprehensive Organic Name Reactions and Reagents, 2010, 1588
E. D. Matveeva, N. S. Zefirov, “On the mechanism of the Kabachnik-Fields reaction: Does a mechanism of nucleophilic amination of α-hydroxyphosphonates exist?”, Dokl Chem, 420:2 (2008), 137
V. A. Alfonsov, “Diastereoselective Synthesis of Enantiopure α-Aminophosphonic Acid Derivatives: Pudovik Reaction in Stereoselective Synthesis (Dedicated to A. N. Pudovik, 1916–2006)”, Phosphorus, Sulfur, and Silicon and the Related Elements, 183:11 (2008), 2637
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