Synthesis of Butenolides by One-Pot Cyclization Reactions of Silyl Enol Ethers with Oxalyl Chloride

Abstract

Oxalyl chloride represents a versatile C₂ building block for cyclization reactions. A variety of cyclization reactions of oxalyl chloride are known which involve the formation of two carbon-heteroatom bonds. In contrast, one-pot cyclizations of oxalyl derivatives which proceed by formation of at least one carbon-carbon bond are more rare. In recent years, a number of such cyclizations have been developed which rely on the reaction of oxalyl chloride with silyl enol ethers. These reactions allow for an efficient synthesis of various oxygen heterocycles, such as γ-alkylidenebutenolides, maleic anhydrides and isotetronic acids. The cyclization reactions, which involve the formation of a carbon-carbon and a carbon-oxygen bond, generally proceed with excellent regioselectivity.

• 1 Introduction

• 2 (Trimethylsilyloxy)alkenes

• 3 1,1-Bis(trimethylsilyloxy)ketene Acetals

• 4 1,3-Bis(trimethylsilyloxy)alk-1-enes

• 5 1,3-Bis(trimethylsilyloxy)buta-1,3-dienes

• 5.1 Optimization

• 5.2 Scope and Limitations

• 5.3 Synthesis of γ-Alkylidenetetronic Acids

• 5.4 Hydrogenation and Kinetic Resolution

• 5.5 Functionalization by Palladium(0)-Catalyzed Reactions

• 5.6 Formal Synthesis of Pulvinic Acids and Related Natural Products

• 5.7 Formal Synthesis of Lucidone and Linderone

• 5.8 1,3-Bis(trimethylsilyloxy)-1,3,6-heptatrienes and
  1,3-Bis(trimethylsilyloxy)-1,3,7-octatrienes

• 5.9 Synthesis of 5-Alkylidene-2,5-dihydropyrrol-2-ones

• 6 Bis- and Tris(silyloxy)trienes

• 6.1 1,5-Bis(trimethylsilyloxy)-1,3,5-hexatrienes

• 6.2 1,3,5-Tris(trimethylsilyloxy)-1,3,5-hexatrienes

• 6.3 2,4-Bis(trimethylsilyloxy)-1,3,5-hexatrienes

• 7 Conclusion

Key words

one-pot cyclization - silyl enol ethers - oxalyl chloride - butenolides - O-heterocycles

References

• 1 For a review of cyclization reactions of bis(imidoyl)di-chlorides of oxalic acid: Langer P. Döring M. Eur. J. Org. Chem.  2002,  221 
• 2a Iida T. Itaya T. Tetrahedron  1993,  49:  10511 
• 2b Skinner GS. Ludwig RE. J. Am. Chem. Soc.  1956,  78:  4656 
• 2c Skinner GS. Perkins JF. J. Am. Chem. Soc.  1950,  72:  5569 
• 2d Markham KR. Rae ID. Aust. J. Chem.  1965,  18:  1497 
• 2e Speziale AJ. Smith LR. J. Org. Chem.  1963,  28:  1805 
• 2f Neidlein R. Arch. Pharm. Ber. Dtsch. Pharm. Ges.  1965,  298:  124 
• 2g Goerdeler J. Schenk H. Chem. Ber.  1965,  98:  2954 
• 2h Goerdeler J. Nandi K. Chem. Ber.  1981,  114:  549 
• 2i Gross H. Zinner G. Chem. Ber.  1973,  106:  2315 
• 2j Ulrich H. Sayigh AAR. J. Org. Chem.  1965,  30:  2781 
• 2k Zaleska B. Trzewik B. Grochowski J. Serda P. Synthesis  2003,  2559 
• 3a Claisen L. Ewan T. Justus Liebigs Ann. Chem.  1895,  284:  245 
• 3b Boothe JH. Wilkinson RG. Kushner S. Williams JH. J. Am. Chem. Soc.  1953,  75:  1732 
• 3c Ojima N. Takenaka S. Seto S. Phytochemistry  1973,  12:  2527 
• 3d Samarian C. Wanzlick H.-W. Tetrahedron Lett.  1974,  24:  2125 
• 3e Trowitzsch W. Justus Liebigs Ann. Chem.  1977,  1707 
• 3f Subramaniam CS. Thomas PJ. Mamdapur VR. Chadha MS. Synthesis  1978,  468 
• 3g Collins PW. Dajani EZ. Pappo R. Gasiecki AF. Bianchi RG. Woods EM. J. Med. Chem.  1983,  26:  786 
• 3h Tanaki K. Okada M. Yamada M. Negoro K. J. Org. Chem.  1982,  47:  1200 
• 4 Langer P. Stoll M. Angew. Chem. Int. Ed.  1999,  38:  1803 ; Angew. Chem. 1999, 111, 1919
• 5a Ziegler E. Eder M. Belegratis C. Prewedourakis E. Monatsh. Chem.  1967,  98:  2249 
• 5b Ziegler E. Kollenz G. Igel H. Monatsh. Chem.  1971,  102:  1769 
• 5c Kollenz G. Kappe CO. Abd el Nabey H. Heterocycles  1991,  32:  669 
• 6a Saalfrank RW. Lutz T. Angew. Chem., Int. Ed. Engl.  1990,  29:  1041 ; Angew. Chem. 1990, 102, 1064
• 6b Saalfrank RW. Lutz T. Hörner B. Gündel J. Peters K. von Schnering HG. Chem. Ber.  1991,  124:  2289 
• 6c Saalfrank RW. Nachtrab J. Reck S. Hampel F. Z. Naturforsch., B: Chem. Sci.  1999,  54:  179 
• 6d For N-heterocycles, see: Saalfrank RW. Hoerner B. Reck S. Nachtrab J. Peters E.-M. Z. Naturforsch., B: Chem. Sci  1996,  51:  1084 
• 7 Sartori G. Bigi F. Canali G. Maggi R. Casnati G. Tao X. J. Org. Chem.  1993,  58:  840 
• 8a Bergman J. Tetrahedron Lett.  1989,  30:  1837 
• 8b Palmisano G. Danieli B. Lesma G. Riva R. J. Org. Chem.  1985,  50:  3322 
• See also:
• 8c Cheng Y. Yang H.-B. Wang M.-X. Williams DJ. Tetrahedron  2002,  58:  2821 
• 8d El-Sayed AM. Allah OAA. Phosphorus, Sulfur Silicon Relat. Elem.  2001,  170:  75 
• 9a Brownbridge P. Synthesis  1983,  1 
• 9b Brownbridge P. Synthesis  1983,  85 
• 10 Langer P. Synthesis  2002,  441 
• 11 Murai S. Hasegawa K. Sonoda N. Angew. Chem., Int. Ed. Engl.  1975,  14:  636 ; Angew. Chem. 1975, 87, 668
• 12 Kappe CO. Kollenz G. Wentrup C. Heterocycles  1994,  38:  779 
• 14 Heurtaux B. Lion C. Le Gall T. Mioskowski C. J. Org. Chem.  2005,  70:  1474 
• 15 Ullah E. Langer P. Synlett  2004,  2782 
• 16 Dede R. Michaelis L. Langer P. Tetrahedron Lett.  2005,  46:  8129 
• 17 Langer P. Schneider T. Stoll M. Chem. Eur. J.  2000,  6:  3204 
• 19 Nguyen VTH. Appel B. Bellur E. Synthesis  2006,  2865 
• 20 Langer P. Saleh NNR. Org. Lett.  2000,  2:  3333 
• 21 Langer P. Saleh NNR. Köhler V. Eur. J. Org. Chem.  2002,  1566 
• 22 Langer P. Eckardt T. Synlett  2000,  844 
• 24 Langer P. Saleh NNR. Köhler V. Eur. J. Org. Chem.  2002,  1566 
• 25 Kirschner A. Langer P. Bornscheuer UT. Tetrahedron: Asymmetry  2004,  15:  2871 
• 26 Langer P. Eckardt T. Schneider T. Göbel C. Herbst-Irmer R. J. Org. Chem.  2001,  66:  2222 
• 27 Ahmed Z. Langer P. J. Org. Chem.  2004,  69:  3753 
• 28 Ahmed Z. Langer P. Eur. J. Org. Chem.  2006,  1057 
• Reviews:
• 29a Rao YS. Chem. Rev.  1976,  76:  625 
• 29b Pattenden G. Prog. Chem. Nat. Prod.  1979,  35:  133 
• 29c Gill M. Steglich W. Prog. Chem. Org. Nat. Prod.  1987,  51:  1 
• 29d Knight DW. Contemp. Org. Synth.  1994,  1:  287 
• 29e Negishi E.-i. Kotora M. Tetrahedron  1997,  53:  6707 
• For reviews of syntheses of g-alkylidenebutenolides, see:
• 29f Brückner R. Chem. Commun.  2002,  141 
• 29g Brückner R. Curr. Org. Chem.  2001,  5:  679 
• 30 Ahmed Z. Langer P. Tetrahedron  2005,  61:  2055 
• 31 Ahmed Z. Albrecht U. Langer P. Eur. J. Org. Chem.  2005,  3469 
• 32a Desage-El Murr M. Nowaczyk S. Le Gall T. Mioskowski C. Amekraz B. Moulin C. Angew. Chem. Int. Ed.  2003,  42:  1289 ; Angew. Chem. 2003, 115, 1327
• 32b Desage-El Murr M. Nowaczyk S. Le Gall T. Mioskowski C. Eur. J. Org. Chem.  2006,  1489 
• 33 Bose G. Langer P. Synlett  2005,  1021 
• 34a Clemo NG. Gedge DR. Pattenden G. J. Chem. Soc., Perkin Trans. 1  1981,  1448 
• 34b Lee H.-H. Que Y.-T. J. Chem. Soc., Perkin Trans. 1  1985,  453 
• 35 Langer P. Eckardt T. Stoll M. Org. Lett.  2000,  2991 
• 36 Haase C. Langer P. Synlett  2005,  453 
• 37 James GD. Mills SD. Pattenden G. J. Chem. Soc., Trans. 1  1993,  2581 
• 38 Langer P. Freifeld I. Synlett  2001,  523 

13

Ullah, E.; Langer, P., unpublished results.

18

Reim, S.; Ahmed, Z.; Langer, P., unpublished results.

23

Nguyen, V. T. H.; Langer, P., unpublished results.