Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2005(16): 2787-2797
DOI: 10.1055/s-2005-872096
DOI: 10.1055/s-2005-872096
PAPER
© Georg Thieme Verlag Stuttgart · New York
Solvent-Free Synthesis of Cyanohydrin Derivatives Catalysed by Triethylamine
Further Information
Received
16 June 2005
Publication Date:
22 July 2005 (online)
Publication History
Publication Date:
22 July 2005 (online)
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
- 1
Tanaka K. Solvent-Free Organic Synthesis Wiley-VCH; Weinheim: 2003. -
2a
Chen F.-X.Feng X. Synlett 2005, 892 -
2b
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 -
2c
Brunel J.-M.Holmes IP. Angew. Chem. Int. Ed. 2004, 43: 2752 -
2d
North M. Tetrahedron: Asymmetry 2003, 14: 147 - 3
Au AT. Synth. Commun. 1984, 14: 743 - 4
Thanasa N.Prachyawarakorn V.Tontoolarug S.Ruchirawat S. Tetrahedron Lett. 2003, 44: 1019 - 5
Shin D.-S.Jung Y.-S.Kim J.-J.Ahn C. Bull. Korean Chem. Soc. 1998, 19: 119 - 6
Scholl M.Lim C.-K.Fu GC. J. Org. Chem. 1995, 60: 6229 - 7
Deardorff DR.Taniguchi CM.Tafti SA.Kim HY.Choi SY.Downey KJ.Nguyen TV. J. Org. Chem. 2001, 66: 7191 - 8
Berthiaume D.Poirier D. Tetrahedron 2000, 56: 5995 - 9
Linghu X.Nicewicz DA.Johnson JS. Org. Lett. 2002, 4: 2957 - 10
Okimoto M.Chiba T. Synthesis 1996, 1188 - 11
Hoffmann HMR.Ismail ZM.Hollweg R.Zein AR. Bull. Chem. Soc. Jpn. 1990, 63: 1807 - 12
Micó I.Nájera C. Tetrahedron 1993, 49: 4327 - 13
Baeza A.Nájera C.Sansano JM. Arkivoc 2005, ix: 353 ; www.arkat-usa.org - For the synthesis of non-racemic O-alkoxycarbonyl cyanohydrins:
-
14a
Tian S.-K.Deng L. J. Am. Chem. Soc. 2001, 123: 6195 -
14b
Tian J.Yamagiwa N.Matsunaga S.Shibasaki M. Angew. Chem. Int. Ed. 2002, 41: 3636 -
14c
Casas J.Baeza A.Sansano JM.Nájera C.Saá JM. Tetrahedron: Asymmetry 2003, 14: 197 -
14d
Belokon’ YN.Blacker AJ.Clutterbuck LA.North M. Org. Lett. 2003, 5: 4505 -
14e
Belokon’ YN.Blacker AJ.Carta P.Clutterbuck LA.North M. Tetrahedron 2004, 60: 10433 -
14f
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:
-
15a
Baeza A.Nájera C.Sansano JM. Tetrahedron: Asymmetry, in press -
15b
Huang W.Song Y.Bai C.Cao G.Zheng Z. Tetrahedron Lett. 2004, 45: 4763 -
15c
Belokon’ YN.Carta P.North M. Lett. Org. Chem. 2004, 1: 81 -
15d
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 -
15e
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:
-
16a
Baeza A.Casas J.Nájera C.Sansano JM.Saá JM. Angew. Chem. Int. Ed. 2003, 42: 3143 -
16b
Abiko Y.Yamagiwa N.Sugita M.Tian J.Matsunaga S.Shibasaki M. Synlett 2004, 2434 -
16c
Baeza A.Nájera C.Sansano JM.Saá JM. Chem. Eur. J. 2005, 11: 3849 - 17
Karini B.Ma’Mani L. Org. Lett. 2004, 6: 4813 - 18
Shen Z.-L.Ji S.-J.Loh T.-P. Tetrahedron Lett. 2005, 46: 3137 -
19a
He B.Li Y.Feng X.Zhang G. Synlett 2004, 1776 -
19b
Okimoto M.Chiba T. Synthesis 1996, 1188 -
19c
Azizi N.Saidi MR. J. Organomet. Chem. 2003, 688: 283 - 20
Iwanami K.Oriyama T. Chem. Lett. 2004, 1324 -
21a
Casas J.Nájera C.Sansano JM.Saá JM. Org. Lett. 2002, 4: 2589 -
21b
Casas J.Nájera C.Sansano JM.Saá JM. Tetrahedron 2004, 60: 10487 -
22a
Gotor V. J. Biotechnol. 2002, 96: 35 -
22b
Gotor V. Org. Process Res. Dev. 2002, 6: 420 - 23
Ling S.-K.Tanaka T.Kouno I. J. Nat. Prod. 2002, 65: 131 -
24a
Cho BT.Kang SK.Shin SH. Tetrahedron: Asymmetry 2002, 13: 1209 -
24b
Brown RFC.Donohue AC.Jackson WR.McCarthy TD. Tetrahedron 1994, 50: 13739 -
24c
Brown RFC.Jackson WR.McCarthy TD. Tetrahedron: Asymmetry 1993, 4: 205 -
25a
Beckmann M.Haack K.-J. Chem. Unserer Zeit 2003, 37: 88 -
25b
Breuer M.Ditrich K.Habicher T.Hauer B.Keβeler M.Stürmer R.Zelinski T. Angew. Chem. Int. Ed. 2004, 43: 788 - 26
van Langen LM.van Rantwijk F.Sheldon RA. Org. Process Res. Dev. 2003, 7: 828 - 27
Duquette J.Zhang M.Zhu L.Reeves RS. Org. Process Res. Dev. 2003, 7: 285 - 28
Johnson DV.Felfer U.Griengl H. Tetrahedron 2000, 56: 781 - 29
Johnson DV.Griengl H. Tetrahedron 1997, 53: 617 - 30
Zha C.Brown GB.Brouillette WJ. J. Med. Chem. 2004, 47: 6519 - 31
Bigg D,Charbier DL,Etienne P,Auvin S, andAnget M. inventors; US Patent 96628276. ; Chem. Abstr. , 127, 684395 - 32
Park D.-S.Peterson C.Zhao S.Coats JR. Pest. Manag. Sci. 2004, 60: 833 -
33a
Matsumoto S.Suzuki M.Kanai M.Shibasaki M. Tetrahedron 2004, 60: 10497 -
33b
Matsumoto S.Suzuki M.Kanai M.Shibasaki M. Tetrahedron Lett. 2002, 43: 8647 - 34
Li Y.He B.Qin B.Feng X.Zhang G. J. Org. Chem. 2004, 69: 7910 - 35
Ryu D.Corey EJ. J. Am. Chem. Soc. 2004, 126: 8106 - 36
Effenberger F.Jäger J. Chem. Eur. J. 1997, 3: 1370 - 37
Yang W.-B.Fang J.-M. J. Org. Chem. 1998, 63: 1356 - 38
Hamashima Y.Kanai M.Shibasaki M. J. Am. Chem. Soc. 2000, 122: 7412 - 39
Masumoto S.Suzuki M.Kanai M.Shibasaki M. Tetrahedron 2004, 60: 10497 - 40
Kruchok IS.Gerus II.Kukhar VP. Tetrahedron 2000, 56: 6533 - 41
Wang Z.Fetterly B.Verkade JG. J. Organomet. Chem. 2002, 646: 161 - 42
Wuts PGM.Ashford SW.Anderson AM.Atkins JR. Org. Lett. 2003, 5: 1483 - 43
Huang W.Song Y.Wang J.Cao G.Zheng Z. Tetrahedron 2004, 60: 10469 - 44
Fadnavis NW.Radhika KR.Kasiraman R.Madhuri KV. Tetrahedron: Asymmetry 2004, 15: 385