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Synthesis 2011(19): 3204-3207  
DOI: 10.1055/s-0030-1260175
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Novel Method for the Stereoselective Synthesis of Thiiran-2-ylmethyl Alkylcarbamates

Andrey Shiryaev*a, Vadim Shiryaeva, Alexander Korlukovb, Daniya Khamitovab
a Samara State Technical University, Galaktionovskaya St. 244, 443100 Samara, Russian Federation
Fax: +7(846)3322122; e-Mail: andrey_shiryaev@yahoo.com;
b Nesmeyanov Institute of Organoelement Compounds, Vavilov St. 28, 119991 Moscow, Russian Federation
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Publikationsverlauf

Received 7 June 2011
Publikationsdatum:
18. August 2011 (online)

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Abstract

A highly efficient stereoselective conversion of N-alkyl-5-(acyloxymethyl)-1,3-oxathiolane-2-imines into thiiran-2-ylmethyl alkylcarbamates is described. The reaction is catalyzed by sodium methoxide and proceeds under mild conditions at room temperature in methanol.

Key words

thiiranes - imines - esters - tandem reaction - stereoselectivity

    References

  • 1 Warkentin J. Plazuk D. In Comprehensive Heterocyclic Chemistry III   Vol. 1:  Katritzky AR. Ramsden CA. Scriven EFV. Taylor RJK. Elsevier; Amsterdam: 2008.  p.299 
    Suche in Google Scholar
  • 2a Cho H.-J. Jung M.-J. Kwon Y. Na Y. Bioorg. Med. Chem. Lett.  2009,  19:  6766 
    Suche in Google Scholar
  • 2b Cho H.-J. Jung M.-J. Woo S. Kim J. Lee E.-S. Kwon Y. Na Y. Bioorg. Med. Chem.  2010,  18:  1010 
    Suche in Google Scholar
  • 3a Huang J. Wang F. Du D.-M. Xu J. Synthesis  2005,  2122 
  • 3b Yu H. Cao S. Zhang L. Liu G. Xu J. Synthesis  2009,  2205 
  • 3c Li X. Xu J. Tetrahedron  2011,  67:  1681 
    Suche in Google Scholar
  • 4a Sander M. Chem. Rev.  1966,  66:  297 
    Suche in Google Scholar
  • 4b Fokin AV. Kolomiets AF. Khimiya Tiiranov (Thiirane Chemistry)   Nuaka; Moscow: 1978.  p.344 
  • 4c Vedejs E. Kraffi GA. Tetrahedron  1982,  38:  2857 
    Suche in Google Scholar
  • 4d Bouda H. Borredon ME. Delman M. Gaset A. Synth. Commun.  1989,  19:  491 
    Suche in Google Scholar
  • 4e Ketcham R. Shah VP. J. Org. Chem.  1963,  28:  229 
    Suche in Google Scholar
  • 5 Korn AC. Morder L. J. Chem. Res., Synop.  1995,  102 
  • 6 Takido T. Kobayashi Y. Itabashi K. Synthesis  1986,  779 
    Thieme Connect
  • 7a Brugat N. Duran J. Polo A. Real J. Alvarez-Larena A. Piniella JF. Tetrahedron: Asymmetry  2002,  13:  569 
    Suche in Google Scholar
  • 7b Harfoushe J. Herault D. Tommasino ML. Pellet-Rostaing S. Lemaire M. Tetrahedron: Asymmetry  2004,  15:  3413 
    Suche in Google Scholar
  • 8a Pederson RL. Liu KK.-C. Rutan JF. Chen L. Wong C.-H. J. Org. Chem.  1990,  55:  4897 
    Suche in Google Scholar
  • 8b Zunszain PA. Varela O. Tetrahedron: Asymmetry  2000,  11:  765 
    Suche in Google Scholar
  • 8c Herault D. Saluzzo C. Lemaire M. Tetrahedron: Asymmetry  2006,  17:  1944 
    Suche in Google Scholar
  • 9a Łukowska E. Plenkiewicz J. Tetrahedron: Asymmetry  2005,  16:  2149 
    Suche in Google Scholar
  • 9b Łukowska E. Plenkiewicz J. Tetrahedron: Asymmetry  2007,  18:  493 
    Suche in Google Scholar
  • 10 Łukowska E. Plenkiewicz J. Tetrahedron: Asymmetry  2007,  18:  1202 
    CrossrefSuche in Google Scholar
  • 11a Shiryaev AK. Moiseev IK. Popov VA. Zh. Org. Khim.  1992,  28:  418 
    Suche in Google Scholar
  • 11b Shiryaev AK. Moiseev IK. Karpeev SS. ARKIVOC  2005,  (iv):  199 
    Suche in Google Scholar
  • 11c Shiryaev AK. Kong Thoo lin P. Moiseev IK. Synthesis  1997,  38 
  • 12 Shiryaev AK. Kryslov IY. Moiseev IK. Zh. Org. Khim.  2000,  36:  458 
    Suche in Google Scholar
  • 13 Shiryaev AK. Zh. Org. Khim.  2003,  39:  1877 
    Suche in Google Scholar
  • 14a Condreay LD. Condreay JP. Jansen RW. Paff MT. Averett DR. Antimicrob. Agents Chemother.  1996,  40:  520 
    Suche in Google Scholar
  • 14b Addor RW. inventors; US Patent  3281430.  ; Chem. Abstr. 1967, 66, 65483s
  • 14c Feinauer R, and Hamann K. inventors; Ger. Patent  1242631.  ; Chem. Abstr. 1968, 68, 21923x
  • 14d Irikuri T, Suzue S, Hasegawa Y, and Kawasaki H. inventors; Jap. Patent  7105698.  ; Chem. Abstr. 1971, 74, 141740f
  • 14e Pflugfelder B. inventors; US Patent  3639610.  ; Chem. Abstr. 1972, 76, 140770v
  • 14f Oyamada K, Nagano M, Tobizuka J, and Matsui K. inventors; Jap. Patent  7246064.  ; Chem. Abstr. 1973, 78, 124598f
  • 14g Sauer W, Goldner H, and Carstens E. inventors; East Ger. Patent  105215.  ; Chem. Abstr. 1974, 81, 151824v
  • 14h Bollinger FG. inventors; Eur. Pat. Appl. EP  11473.  ; Chem. Abstr. 1981, 94, 175100a
  • 15a Wagner-Jauregg T. Häring M. Helv. Chim. Acta  1958,  41:  377 
    Suche in Google Scholar
  • 15b Hayashi T. Bull. Chem. Soc. Jpn.  1972,  45:  1507 
    Suche in Google Scholar
  • 16a Aragozzini F. Maconi E. Potenza D. Scolastico C. Synthesis  1989,  225 
  • 16b Chavre SN. Choo H. Cha JH. Pae AN. Choi KI. Cho YS. Org. Lett.  2006,  8:  3617 
    Suche in Google Scholar
  • 17 Wilson SM. Wiberg KB. Cheeseman JR. Frisch MJ. Vaccaro PH. J. Phys. Chem. A  2005,  109:  11752 
    CrossrefSuche in Google Scholar
  • 18 Autschbach J. Chirality  2009,  21:  E116 
    CrossrefSuche in Google Scholar
  • 19 Chen Y. Porco JA. Panek JS. Org. Lett.  2007,  9:  1529 
    CrossrefSuche in Google Scholar
  • 20 Kalicki P. Karchier M. Michalak K. Wicha J. J. Org. Chem.  2010,  75:  5388 
    CrossrefSuche in Google Scholar
  • 21 Frisch MJ. Trucks GW. Schlegel HB. Scuseria GE. Robb MA. Cheeseman JR. Scalmani G. Barone V. Mennucci B. Petersson GA. Nakatsuji H. Caricato M. Li X. Hratchian HP. Izmaylov AF. Bloino J. Zheng G. Sonnenberg JL. Hada M. Ehara M. Toyota K. Fukuda R. Hasegawa J. Ishida M. Nakajima T. Honda Y. Kitao O. Nakai H. Vreven T. Montgomery Jr. JA. Peralta JE. Ogliaro F. Bearpark M. Heyd JJ. Brothers E. Kudin KN. Staroverov VN. Kobayashi R. Normand J. Raghavachari K. Rendell A. Burant JC. Iyengar SS. Tomasi J. Cossi M. Rega N. Millam NJ. Klene M. Knox JE. Cross JB. Bakken V. Adamo C. Jaramillo J. Gomperts R. Stratmann RE. Yazyev O. Austin AJ. Cammi R. Pomelli C. Ochterski JW. Martin RL. Morokuma K. Zakrzewski VG. Voth GA. Salvador P. Dannenberg JJ. Dapprich S. Daniels AD. Farkas Ö. Foresman JB. Ortiz JV. Cioslowski J. Fox DJ. Gaussian 09, Revision A.1   Gaussian Inc.; Wallingford (CT): 2009. 
  • 22 Schaus SE. Brandes BD. Larrow JF. Tokunaga M. Hansen KB. Gould AE. Furrow ME. Jacobsen EN. J. Am. Chem. Soc.  2002,  124:  1307 
    CrossrefPubMedSuche in Google Scholar
  • 23 Lok CM. Ward JP. van Dorp DA. Chem. Phys. Lipids  1976,  16:  115 
    CrossrefSuche in Google Scholar