A Novel Approach to γ-Hydroxy-α,β-unsaturated
Compounds

Henryk Krawczyk; Katarzyna Wąsek; Jacek Kędzia

doi:10.1055/s-0028-1083162

PAPER

A Novel Approach to γ-Hydroxy-α,β-unsaturated Compounds

Henryk Krawczyk*, Katarzyna Wąsek, Jacek Kędzia
Institute of Organic Chemistry, Technical University of Łódź, Żeromskiego 116, 90-924 Łódź, Poland
Fax: +48(42)6365530; e-Mail: henkrawc@p.lodz.pl;

Abstract

Alle Artikel dieser Rubrik

Abstract

A simple synthesis of (E)-alk-1-enyl mesylates from (E)-alk-1-enylphosphonates is reported. Construction of γ-hydroxy-α,β-unsaturated compounds was achieved by a two-step process involving dihydroxylation of the enol mesylates followed by HWE reaction of the resulting α-hydroxy aldehydes with activated methylphosphonates. Enantioselective synthesis of the title compounds is also reported.

Key words

alk-1-enyl mesylates - dihydroxylation - α-hydroxy aldehydes - Horner-Wadsworth-Emmons reaction - Conant-Swan fragmentation

Volltext

Referenzen

References

1a Trost BM. Rigby JH. J. Org. Chem. 1978, 43: 2938

1b Bartlett PA. Green FRIII. J. Am. Chem. Soc. 1978, 100: 4858

1c Corey EI. Carpino P. Tetrahedron Lett. 1990, 31: 7555

1d Nokami J. Ohkura M. Dan-oh Y. Sakamoto Y. Tetrahedron Lett. 1991, 32: 2409

1e Burgess K. Cassidy J. Henderson I. J. Org. Chem. 1991, 56: 2050

1f Tian J. Yamagiwa N. Matsunaga S. Shibasaki M. Org. Lett. 2003, 3: 3021

1g Trost BM. Dong L. Schroeder GM. J. Am. Chem. Soc. 2005, 127: 10259

1h Trost BM. Dong L. Schroeder GM. J. Am. Chem. Soc. 2005, 127: 2844

1i Takemura A. Fujuwara K. Shimawaki K. Murai A. Kawai H. Suzuki T. Tetrahedron 2005, 61: 7392

2 Nokami J. Taniguchi A. Honda M. Fututake S. Chem. Lett. 1995, 1025

3a Cass QB. Jaxa-Chamiec AA. Sammes PG. J. Chem. Soc., Chem. Commun. 1981, 1248

3b Tanikaga R. Nozaki Y. Tanaka K. Kaji A. Chem. Lett. 1982, 1703

3c Tanikaga R. Nozaki Y. Tamura T. Kaji A. Synthesis 1983, 134

3d Nokami J. Mandai T. Ikamura Y. Nishiuchi K. Kawada M. Wakabayashi S. Tetrahedron Lett. 1981, 22: 4489

3e Ono T. Tamaoka T. Yuasa Y. Matsuda T. Nokami J. Wakabayashi S. J. Am. Chem. Soc. 1984, 106: 7890

3f Trost BM. Tometzki GB. Synthesis 1991, 1235

4a Kosugi H. Kitaoka M. Takayashi A. Uda H. J. Chem. Soc., Chem. Commun. 1986, 1286

4b Burgess K. Henderson I. Tetrahedron: Asymmetry 1990, 1: 57

4c Trost BM. Mallart S. Tetrahedron Lett. 1993, 34: 8025

4d Nokami J. Mandai T. Nishimura A. Takeda T. Wakabayashi S. Tetrahedron Lett. 1986, 27: 5109

5 Matsushita Y. Sugamoto K. Nakama T. Sakamoto T. Matsui T. Tetrahedron Lett. 1995, 36: 1879

6a Tiecco M. Testaferri L. Tingoli M. Bagnoli L. Santi C. J. Chem. Soc., Chem. Commun. 1993, 637

6b Tiecco M. Testaferri L. Marini F. Santi C. Bagnoli L. Temperini A. Tetrahedron: Asymmetry 1999, 10: 747

7 Fleming FF. Gudipati V. Steward OW. Org. Lett. 2002, 4: 659

8a Tanikaga R. Hosoya K. Kaji A. Chem. Lett. 1987, 829

8b Kang S.-K. Lee D.-H. Kim Y.-SC. Kang S.-C. Synth. Commun. 1992, 22: 1109

9a Kitano Y. Matsumoto T. Wakasa T. Okamoto S. Shimazaki T. Kobayashi Y. Sato F. Miyaji K. Arai K. Tetrahedron Lett. 1987, 28: 6351

9b Yamakawa I. Urabe H. Kobayashi Y. Sato F. Tetrahedron Lett. 1991, 32: 2045

9c Ostwald R. Chavant P.-Y. Stadtmuller H. Knochel P. J. Org. Chem. 1994, 59: 4143

10a Baeza A. Casas J. Najera C. Sansano JM. J. Org. Chem. 2006, 71: 3837

10b Perrone S. Metzger A. Knochel P. Synlett 2007, 1047

11 Rodriguez S. Kneeteman M. Izquierdo J. López I. González FV. Peris G. Tetrahedron 2006, 62: 11112

12a Thijs L. Dommerholt FJ. Leemhuis FMC. Zwanenburg B. Tetrahedron Lett. 1990, 31: 6589

12b Bernardi A. Cardani S. Scolastico C. Villa R. Tetrahedron 1988, 44: 491

13 Evans P. Leffray M. Tetrahedron 2003, 59: 7973

14 Speck JC. Adv. Carbohydr. Chem. 1958, 13: 64

15a Sauer JC. Wilson JDC. J. Am. Chem. Soc. 1955, 77: 3793

15b Rappoport Z. Topol A. J. Chem. Soc., Perkin. Trans. 2 1972, 1823

15c Hirsch E. Hünig S. Reissig H.-U. Chem. Ber. 1982, 115: 3687

15d Buchanan JG. Craven DA. Wightman RH. Harnden MR. J. Chem. Soc., Perkin Trans. 1 1991, 195

15e Marino JP. Laborde E. Paley RS. J. Am. Chem. Soc. 1988, 110: 966

15f Marino JP. Laborde E. Deering CF. Paley RS. Ventura MP. J. Org. Chem. 1994, 59: 3193

15g Acherki H. Alvarez-Ibarra C. de-Dios A. Quiroga ML. Tetrahedron 2002, 58: 3217

16 Waszkuć W. Janecki T. Bodalski R. Synthesis 1984, 1025

17 Fürst A. Koller F. Helv. Chim. Acta 1947, 30: 1454

18 McKenna CE. Schmidhauser J. J. Chem. Soc., Chem. Commun. 1979, 739

19a Conant JB. Cook AA. J. Am. Chem. Soc. 1920, 42: 830

19b Conant JB. Jackson EL. J. Am. Chem. Soc. 1924, 46: 1003

19c Maynard JA. Swan JM. Proc. Chem. Soc. 1963, 61

19d Maynard JA. Swan JM. Aust. J. Chem. 1963, 16: 596

20 Kolb HC. VanNieuwenhze MS. Sharpless KB. Chem. Rev. 1994, 94: 2483