Synthesis 2018; 50(22): 4476-4482
DOI: 10.1055/s-0036-1591597
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis of (Z)-2-[(tert-Butyldimethylsilyl)oxy]-3-(phenylthio) acrylaldehyde

Michael Topinka
Department of Chemistry, University of Missouri-Columbia, 601 South College Avenue, Columbia, MO 65211, USA   Email: harmatam@missouri.edu
,
Michael Harmata*
Department of Chemistry, University of Missouri-Columbia, 601 South College Avenue, Columbia, MO 65211, USA   Email: harmatam@missouri.edu
› Author Affiliations
This work was supported by the National Science Foundation (CHE-1463724).
Further Information

Publication History

Received: 28 April 2018

Accepted after revision: 05 June 2018

Publication Date:
17 July 2018 (eFirst)

Dedicated to Professor Scott E. Denmark on the occasion of his 65th birthday.

Published as part of the Special Section dedicated to Scott E. Denmark on the occasion of his 65th birthday.

Abstract

The title compound was prepared from ethyl acrylate over seven steps. En route, an ester was prepared that could be catalytically activated with Sc(OTf)3 to undergo a (4+3) cycloaddition with 2,5-dimethylfuran. The title compound reacts with organolithium species and the resultant alkoxide can be trapped as an ester or allowed to experience a silyl shift to produce a highly functionalized ketone.

Supporting Information

 
  • References

    • 1a Oikawa H. Cell Chem. Biol. 2016; 23: 429
    • 1b Gallier F. Curr. Org. Chem. 2016; 20: 2222
    • 1c Bouchez LC. Rusch M. Larraufie M.-H. Curr. Org. Chem. 2016; 20: 2358
    • 1d Gregoritza M. Brandl FP. Eur. J. Pharm. Biopharm. 2015; 97: 438
    • 1e Tanner D. Ascic E. Intramolecular and Transannular Diels–Alder Reactions . In Comprehensive Organic Synthesis II . Knochel P. Elsevier; Amsterdam: 2014. 2nd ed., Vol. 5 466-517
    • 1f Ishihara K. Sakakura A. Intermolecular Diels–Alder Reactions . In Comprehensive Organic Synthesis II . Knochel P. Elsevier; Amsterdam: 2014. 2nd ed., Vol. 5 351-408
    • 2a Wei Y. Shi M. Org. Chem. Front. 2017; 4: 1876
    • 2b Hullaert J. Denoo B. Christiaens M. Callebaut B. Winne JM. Synlett 2017; 28: 2345
    • 2c Li H. Wu J. Synthesis 2015; 47: 22
    • 2d Baunach M. Hertweck C. Angew. Chem. Int. Ed. 2015; 54: 12550
    • 2e Yamago S. Nakamura E. Org. React. 2002; 61: 1
    • 4a Sasaki T. Ishibashi Y. Ohno M. Tetrahedron Lett. 1982; 23: 1693
    • 4b Blackburn C. Childs RF. Kennedy RA. Can. J. Chem. 1983; 61: 1981
  • 5 Harmata M. Sharma U. Org. Lett. 2000; 2: 2703
    • 6a Nilson MG. Funk RL. J. Am. Chem. Soc. 2011; 133: 12451
    • 6b Aungst RA. Jr. Funk RL. Org. Lett. 2001; 3: 3553
    • 7a Keiko NA. Funtikova EA. Stepanova LG. Chuvashev YA. Larina LI. ARKIVOC 2001; (ix): 67
    • 7b Watanabe M. Tsukazaki M. Hirakawa Y. Iwao M. Furukawa S. Chem. Pharm. Bull. 1989; 37: 2914
    • 7c Esswein A. Betz R. Schmidt RR. Helv. Chim. Acta 1989; 72: 213
    • 7d Iwao M. Kuraishi T. Tetrahedron Lett. 1985; 26: 6213
  • 8 Domon K. Tanino K. Kuwajima I. Synlett 1996; 157
  • 9 Ochiai B. Hirano T. Heterocycles 2014; 89: 487
  • 10 Harmata M. Jones DE. Tetrahedron Lett. 1996; 37: 783
  • 11 Frigerio M. Santagostino M. Sputore S. Palmisano G. J. Org. Chem. 1995; 60: 7272