Solvent-Free Synthesis of Cyanohydrin Derivatives Catalysed by Triethylamine

Alejandro Baeza; Carmen Nájera; Mª  de Gracia Retamosa; José M. Sansano

doi:10.1055/s-2005-872096

PAPER

Solvent-Free Synthesis of Cyanohydrin Derivatives Catalysed by Triethylamine

Alejandro Baeza, Carmen Nájera*, Mª de Gracia Retamosa, José M. Sansano
Departamento de Química Orgánica and Instituto de Síntesis Orgánica (ISO), Facultad de Ciencias, Universidad de Alicante, Apdo. 99, 03080-Alicante, Spain
Fax: +34(96)5903549; e-Mail: cnajera@ua.es;

Abstract

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Abstract

A very simple one-step environmentally friendly procedure for the synthesis of O-substituted cyanohydrins from aldehydes and ketones, in the absence of solvent, employing minimum amounts of the corresponding cyanides has been optimised. Aldehydes react more rapidly than ketones using triethylamine as catalyst offering in both cases almost quantitative yields of the corresponding O-trimethylsilyl, O-methoxycarbonyl, O-benzoyl and O-acetyl cyanohydrins.

Key words

addition reactions - catalysis - cyanohydrin derivatives - green chemistry - solvent-free reactions

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References

<A NAME="RZ11805SS-1">1</A> Tanaka K. Solvent-Free Organic Synthesis Wiley-VCH; Weinheim: 2003.

<A NAME="RZ11805SS-2A">2a</A> Chen F.-X. Feng X. Synlett 2005, 892

<A NAME="RZ11805SS-2B">2b</A> Synthesis and Applications of Non-Racemic Cyanohydrins and α-Amino Acids, Tetrahedron Symposium in Print Vol. 60: North M. Elsevier; London: 2004. p.10371-10568

<A NAME="RZ11805SS-2C">2c</A> Brunel J.-M. Holmes IP. Angew. Chem. Int. Ed. 2004, 43: 2752

<A NAME="RZ11805SS-2D">2d</A> North M. Tetrahedron: Asymmetry 2003, 14: 147

<A NAME="RZ11805SS-3">3</A> Au AT. Synth. Commun. 1984, 14: 743

<A NAME="RZ11805SS-4">4</A> Thanasa N. Prachyawarakorn V. Tontoolarug S. Ruchirawat S. Tetrahedron Lett. 2003, 44: 1019

<A NAME="RZ11805SS-5">5</A> Shin D.-S. Jung Y.-S. Kim J.-J. Ahn C. Bull. Korean Chem. Soc. 1998, 19: 119

<A NAME="RZ11805SS-6">6</A> Scholl M. Lim C.-K. Fu GC. J. Org. Chem. 1995, 60: 6229

<A NAME="RZ11805SS-7">7</A> Deardorff DR. Taniguchi CM. Tafti SA. Kim HY. Choi SY. Downey KJ. Nguyen TV. J. Org. Chem. 2001, 66: 7191

<A NAME="RZ11805SS-8">8</A> Berthiaume D. Poirier D. Tetrahedron 2000, 56: 5995

<A NAME="RZ11805SS-9">9</A> Linghu X. Nicewicz DA. Johnson JS. Org. Lett. 2002, 4: 2957

<A NAME="RZ11805SS-10">10</A> Okimoto M. Chiba T. Synthesis 1996, 1188

<A NAME="RZ11805SS-11">11</A> Hoffmann HMR. Ismail ZM. Hollweg R. Zein AR. Bull. Chem. Soc. Jpn. 1990, 63: 1807

<A NAME="RZ11805SS-12">12</A> Micó I. Nájera C. Tetrahedron 1993, 49: 4327

<A NAME="RZ11805SS-13">13</A> Baeza A. Nájera C. Sansano JM. Arkivoc 2005, ix: 353 ; www.arkat-usa.org

For the synthesis of non-racemic O-alkoxycarbonyl cyanohydrins:

<A NAME="RZ11805SS-14A">14a</A> Tian S.-K. Deng L. J. Am. Chem. Soc. 2001, 123: 6195

<A NAME="RZ11805SS-14B">14b</A> Tian J. Yamagiwa N. Matsunaga S. Shibasaki M. Angew. Chem. Int. Ed. 2002, 41: 3636

<A NAME="RZ11805SS-14C">14c</A> Casas J. Baeza A. Sansano JM. Nájera C. Saá JM. Tetrahedron: Asymmetry 2003, 14: 197

<A NAME="RZ11805SS-14D">14d</A> Belokon’ YN. Blacker AJ. Clutterbuck LA. North M. Org. Lett. 2003, 5: 4505

<A NAME="RZ11805SS-14E">14e</A> Belokon’ YN. Blacker AJ. Carta P. Clutterbuck LA. North M. Tetrahedron 2004, 60: 10433

<A NAME="RZ11805SS-14F">14f</A> Yamagiwa N. Tian J. Matsunaga S. Shibasaki M. J. Am. Chem. Soc. 2005, 127: 3413

For the synthesis of non-racemic O-acyl or O-benzoyl cyanohydrins, see:

<A NAME="RZ11805SS-15A">15a</A> Baeza A. Nájera C. Sansano JM. Tetrahedron: Asymmetry, in press

<A NAME="RZ11805SS-15B">15b</A> Huang W. Song Y. Bai C. Cao G. Zheng Z. Tetrahedron Lett. 2004, 45: 4763

<A NAME="RZ11805SS-15C">15c</A> Belokon’ YN. Carta P. North M. Lett. Org. Chem. 2004, 1: 81

<A NAME="RZ11805SS-15D">15d</A> Belokon’ YN. Carta P. Gutnov AV. Maleev V. Moskalenko MA. Yashkina LV. Ikonnikov NS. Voskoboev NV. Khrustalev VN. North M. Helv. Chim. Acta 2002, 85: 3301

<A NAME="RZ11805SS-15E">15e</A> Belokon’ YN. Gutnov AV. Moskalenko MA. Yashkina LV. Lesovoy DE. Ikonnikov NS. Larichev VS. North M. Chem. Commun. 2002, 244

For the synthesis of non-racemic cyanohydrin O-phosphates, see:

<A NAME="RZ11805SS-16A">16a</A> Baeza A. Casas J. Nájera C. Sansano JM. Saá JM. Angew. Chem. Int. Ed. 2003, 42: 3143

<A NAME="RZ11805SS-16B">16b</A> Abiko Y. Yamagiwa N. Sugita M. Tian J. Matsunaga S. Shibasaki M. Synlett 2004, 2434

<A NAME="RZ11805SS-16C">16c</A> Baeza A. Nájera C. Sansano JM. Saá JM. Chem. Eur. J. 2005, 11: 3849

<A NAME="RZ11805SS-17">17</A> Karini B. Ma’Mani L. Org. Lett. 2004, 6: 4813

<A NAME="RZ11805SS-18">18</A> Shen Z.-L. Ji S.-J. Loh T.-P. Tetrahedron Lett. 2005, 46: 3137

<A NAME="RZ11805SS-19A">19a</A> He B. Li Y. Feng X. Zhang G. Synlett 2004, 1776

<A NAME="RZ11805SS-19B">19b</A> Okimoto M. Chiba T. Synthesis 1996, 1188

<A NAME="RZ11805SS-19C">19c</A> Azizi N. Saidi MR. J. Organomet. Chem. 2003, 688: 283

<A NAME="RZ11805SS-20">20</A> Iwanami K. Oriyama T. Chem. Lett. 2004, 1324

<A NAME="RZ11805SS-21A">21a</A> Casas J. Nájera C. Sansano JM. Saá JM. Org. Lett. 2002, 4: 2589

<A NAME="RZ11805SS-21B">21b</A> Casas J. Nájera C. Sansano JM. Saá JM. Tetrahedron 2004, 60: 10487

<A NAME="RZ11805SS-22A">22a</A> Gotor V. J. Biotechnol. 2002, 96: 35

<A NAME="RZ11805SS-22B">22b</A> Gotor V. Org. Process Res. Dev. 2002, 6: 420

<A NAME="RZ11805SS-23">23</A> Ling S.-K. Tanaka T. Kouno I. J. Nat. Prod. 2002, 65: 131

<A NAME="RZ11805SS-24A">24a</A> Cho BT. Kang SK. Shin SH. Tetrahedron: Asymmetry 2002, 13: 1209

<A NAME="RZ11805SS-24B">24b</A> Brown RFC. Donohue AC. Jackson WR. McCarthy TD. Tetrahedron 1994, 50: 13739

<A NAME="RZ11805SS-24C">24c</A> Brown RFC. Jackson WR. McCarthy TD. Tetrahedron: Asymmetry 1993, 4: 205

<A NAME="RZ11805SS-25A">25a</A> Beckmann M. Haack K.-J. Chem. Unserer Zeit 2003, 37: 88

<A NAME="RZ11805SS-25B">25b</A> Breuer M. Ditrich K. Habicher T. Hauer B. Keβeler M. Stürmer R. Zelinski T. Angew. Chem. Int. Ed. 2004, 43: 788

<A NAME="RZ11805SS-26">26</A> van Langen LM. van Rantwijk F. Sheldon RA. Org. Process Res. Dev. 2003, 7: 828

<A NAME="RZ11805SS-27">27</A> Duquette J. Zhang M. Zhu L. Reeves RS. Org. Process Res. Dev. 2003, 7: 285

<A NAME="RZ11805SS-28">28</A> Johnson DV. Felfer U. Griengl H. Tetrahedron 2000, 56: 781

<A NAME="RZ11805SS-29">29</A> Johnson DV. Griengl H. Tetrahedron 1997, 53: 617

<A NAME="RZ11805SS-30">30</A> Zha C. Brown GB. Brouillette WJ. J. Med. Chem. 2004, 47: 6519

<A NAME="RZ11805SS-31">31</A> Bigg D, Charbier DL, Etienne P, Auvin S, and Anget M. inventors; US Patent 96628276. ; Chem. Abstr. , 127, 684395

<A NAME="RZ11805SS-32">32</A> Park D.-S. Peterson C. Zhao S. Coats JR. Pest. Manag. Sci. 2004, 60: 833

<A NAME="RZ11805SS-33A">33a</A> Matsumoto S. Suzuki M. Kanai M. Shibasaki M. Tetrahedron 2004, 60: 10497

<A NAME="RZ11805SS-33B">33b</A> Matsumoto S. Suzuki M. Kanai M. Shibasaki M. Tetrahedron Lett. 2002, 43: 8647

<A NAME="RZ11805SS-34">34</A> Li Y. He B. Qin B. Feng X. Zhang G. J. Org. Chem. 2004, 69: 7910

<A NAME="RZ11805SS-35">35</A> Ryu D. Corey EJ. J. Am. Chem. Soc. 2004, 126: 8106

<A NAME="RZ11805SS-36">36</A> Effenberger F. Jäger J. Chem. Eur. J. 1997, 3: 1370

<A NAME="RZ11805SS-37">37</A> Yang W.-B. Fang J.-M. J. Org. Chem. 1998, 63: 1356

<A NAME="RZ11805SS-38">38</A> Hamashima Y. Kanai M. Shibasaki M. J. Am. Chem. Soc. 2000, 122: 7412

<A NAME="RZ11805SS-39">39</A> Masumoto S. Suzuki M. Kanai M. Shibasaki M. Tetrahedron 2004, 60: 10497

<A NAME="RZ11805SS-40">40</A> Kruchok IS. Gerus II. Kukhar VP. Tetrahedron 2000, 56: 6533

<A NAME="RZ11805SS-41">41</A> Wang Z. Fetterly B. Verkade JG. J. Organomet. Chem. 2002, 646: 161

<A NAME="RZ11805SS-42">42</A> Wuts PGM. Ashford SW. Anderson AM. Atkins JR. Org. Lett. 2003, 5: 1483

<A NAME="RZ11805SS-43">43</A> Huang W. Song Y. Wang J. Cao G. Zheng Z. Tetrahedron 2004, 60: 10469

<A NAME="RZ11805SS-44">44</A> Fadnavis NW. Radhika KR. Kasiraman R. Madhuri KV. Tetrahedron: Asymmetry 2004, 15: 385