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Synthesis 2013; 45(9): 1215-1226
DOI: 10.1055/s-0032-1318309
DOI: 10.1055/s-0032-1318309
paper
Two-Stage Synthesis of 3-(Perfluoroalkyl)-Substituted Vinyldiazocarbonyl Compounds and Their Nonfluorinated Counterparts: A Comparative Study
Further Information
Publication History
Received: 17 December 2012
Accepted after revision: 04 February 2013
Publication Date:
04 April 2013 (online)
Abstract
Two approaches for the synthesis of fluorinated (F) and nonfluorinated (H) 4-(alkoxycarbonyl)-substituted cis- and trans-vinyldiazocarbonyl compounds with substituents of variable stereoelectronic nature (H, Me, Ph, CF3, OTBS) at the C-3 atom of the vinyl double bond from the relevant 1,3-dicarbonyl compounds were compared: a pathway using the Wittig reaction followed by a diazo transfer reaction was most efficient for the synthesis of the H-vinyldiazocarbonyl compounds (total yields of up to 60%), while the yields of their F-analogues under similar conditions did not exceed 16–37%. An approach via diazo transfer followed by the Wittig reaction, in contrast, is more effective for the preparation of F-vinyldiazocarbonyl compounds (total yields 37–69%). The configuration of the resulting F- and H-vinyldiazocarbonyl compounds is evidently controlled by the steric bulk of the substituent at the C-3 atom of the vinyl double bond and, in addition, depends on the specific synthetic pathway.
Key words
(perfluoroalkyl)-containing vinyldiazocarbonyl compounds - diazo transfer - Wittig reaction - 1,3-diketonesSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
-
References
- 1a Davies HM. L. Aldrichimica Acta 1997; 30: 107
- 1b Davies HM. L. Curr. Org. Chem. 1998; 2: 463
- 2a Zhang Y, Kubicki J, Platz MS. J. Am. Chem. Soc. 2009; 131: 13602
- 2b Freeman PK. J. Org. Chem. 2009; 74: 830
- 2c Moss RA, Tian J, Sauers RR, Sheridan RS, Bhakta A, Zuev RS. Org. Lett. 2005; 7: 4645
- 3a Doyle MP, McKervey MA, Ye T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds: From Cyclopropanes to Ylides. Wiley; New York: 1998: 652
- 3b Hamaguchi M, Matsubara H, Nagai T. J. Org. Chem. 2001; 66: 5395
- 3c Hamaguchi M, Takahashi K, Oshima T, Tamura H. Tetrahedron Lett. 2003; 44: 4339
- 4a Closs GL, Closs LE. J. Am. Chem. Soc. 1961; 83: 2015
- 4b Pincock JA, Mathur NC. J. Org. Chem. 1982; 47: 3699
- 4c Price DJ, Jonson RP. J. Am. Chem. Soc. 1985; 107: 2187
- 5a Davies HM. L, Clark DM, Alligood DB, Eiband GR. Tetrahedron 1987; 43: 4265
-
5b Davies HM. L, Ahmed G, Churchill MR. J. Am. Chem. Soc. 1996; 118: 10774
- 5c Davies HM. L, Calvo R, Ahmed G. Tetrahedron Lett. 1997; 38: 1737
- 5d Davies HM. L. Adv. Cycloaddit. 1999; 5: 119
-
5e Reddy RP, Davies HM. L. J. Am. Chem. Soc. 2007; 129: 10312
- 6a Nikolaev VA, Zakharova VM, Hennig L. J. Fluorine Chem. 2007; 128: 507
- 6b Supurgibekov MB, Hennig L, Schulze B, Nikolaev VA. Russ. J. Org. Chem. 2008; 44: 1840
- 6c Supurgibekov MB, Zakharova VM, Sieler J, Nikolaev VA. Tetrahedron Lett. 2011; 52: 341
- 7 From hereon, we use the ‘cis’ and ‘trans’ designation of spatial arrangement of functional groups (CO2Alk, CN2) around the vinyl double bond, ignoring the priority of the CF3 substituent, since application of the IUPAC Z,E nomenclature in this case implies the same Z or E symbols for (fluoroalkyl)-containing and fluorine-free vinyl substrates with opposite configuration.
- 8a Regitz M. Angew. Chem., Int. Ed. Engl. 1967; 6: 733
- 8b Regitz M, Maas G. Diazo Compounds. Properties and Synthesis . Academic Press; New York: 1986: 596
- 8c Maas G. Angew. Chem. 2009; 121: 8332
- 9 For uniformity in the names of the targeted compounds (2-vinyldiazocarbonyl compounds) and their precursors (allylcarbonyl compounds), for the latter we use the term ‘vinyl’ instead of ‘allyl’ as recommended by the IUPAC rules.
- 10a Baum JS, Shook DA, Davies HM. L, Smith HD. Synth. Commun. 1987; 17: 1709
- 10b Davies HM. L, Saikali E, Clark TJ, Chee EH. Tetrahedron Lett. 1990; 31: 6299
- 10c Nikolaev VA, Kantin GP, Utkin PYu. Russ. J. Org. Chem. 1994; 30: 1354
- 10d Nikolaev VA, Kantin GP. Russ. J. Org. Chem. 2000; 36: 486
- 11a Guillaume M, Janousek Z, Viehe HG. Synthesis 1995; 920
- 11b Poschenrieder H, Stachel H. J. Heterocycl. Chem. 1995; 32: 1457
- 11c Zakharova VM, Hennig L, Nikolaev VA. Synthesis 2005; 2871
- 11d Galiullina SV, Zakharova VM, Kantin GP, Nikolaev VA. Russ. J. Org. Chem. 2007; 43: 607
- 12a Lohaus G, Friedrich W, Jeschke JP. Chem. Ber. 1967; 100: 658
- 12b McIntosh CL, Chapman OL. J. Am. Chem. Soc. 1973; 95: 247
- 12c Alkony I. Chem. Ber. 1965; 98: 3099
- 12d Apparao S, Datta A, Ila H, Junjappa H. Synthesis 1985; 169
- 12e Guandalinia L, Deia S, Gualtieria F, Romanellia MN, Scapecchia S, Teodoria E, Varani K. Helv. Chim. Acta 2002; 85: 96
- 12f Chen L, Huang L, Zhang P. J. Org. Chem. 2003; 68: 5925
- 13 Mawaziny S, Lakani AM. Chim. Chron. 1996; 25: 215
- 14 Cherry K, Parrain JL, Thibonnet J, Duchene A, Abarbri M. J. Org. Chem. 2005; 70: 6669
- 15a Bestman HJ, Kratzer O. Chem. Ber. 1962; 95: 1894
- 15b Johnson AW, LaCount RB. Tetrahedron 1960; 9: 130
- 16 Lombardo L, Mander LN. Synthesis 1980; 368
- 17 Weygand F, Schwenke W, Bestmann HJ. Angew. Chem. 1958; 70: 506
- 18a Regitz M, Bartz W. Chem. Ber. 1970; 103: 1477
- 18b Popik VV, Nikolaev VA. J. Chem. Soc., Perkin Trans. 2 1993; 1971
- 18c Nikolaev VA, Ivanov AV, Shakhmin AA, Sieler J, Rodina LL. Tetrahedron Lett. 2012; 53: 3095
- 19 Peng C, Cheng J, Wang J. J. Am. Chem. Soc. 2007; 129: 8708
- 20a Nikolaev VA, Zhdanova OV, Korobitsyna IK. J. Org. Chem. USSR 1982; 18: 488
- 20b Padwa A, Kulkarni YS, Zhang Z. J. Org. Chem. 1990; 55: 4144
- 20c Davies HM. L, Hougland PW, Cantrell WR. Synth. Commun. 1992; 22: 971
- 20d Shi WF, Ma M, Wang JB. Chin. Chem. Lett. 2004; 15: 911
- 21a Davies HM. L, Hu B. Heterocycles 1993; 35: 385
- 21b Nadeau E, Ventura DL, Brekan JA, Davies HM. L. J. Org. Chem. 2010; 75: 1927
- 22a Boutagy J, Thomas R. Chem. Rev. 1974; 74: 87
- 22b Wadsworth WS. Org. React. 1977; 25: 73
- 22c Maryanoff BE, Reitz AB. Chem. Rev. 1989; 89: 863
- 23a Van Staden LF, Gravestock D, Ager DJ. Chem. Soc. Rev. 2002; 31: 195
- 23b Kano N, Kawashima T. Modern Carbonyl Olefination . Takeda T. Wiley-VCH; Weinheim: 2004: 18
- 23c Korotchenko VN, Nenajdenko VG, Balenkova ES, Shastin AV. Russ. Chem. Rev. 2004; 73: 957
- 23d Ager DJ. Org. React. 1990; 38: 162
- 24 Sano S, Teranishi R, Nagao Y. Tetrahedron Lett. 2002; 43: 9183
- 25 Still WC, Gennari C. Tetrahedron Lett. 1983; 24: 4405
- 26a Motoyoshiya J. Trends Org. Chem. 1998; 7: 63
- 26b Edmonds M, Abell A. Modern Carbonyl Olefination . Takeda T. Wiley-VCH; Weinheim: 2004: 1
- 27 Blanchette MA, Choy W, Davis JT, Essenfeld AP, Masamune S, Roush WR, Sakai T. Tetrahedron Lett. 1984; 25: 2183
- 28 Gillies MB, Tonder JE, Tanner D, Norrby P. J. Org. Chem. 2002; 67: 7378
- 29a Wittig G, Schlosser M. Tetrahedron 1962; 18: 1023
- 29b Märkl G. Tetrahedron Lett. 1961; 807
- 29c Märkl G. Tetrahedron Lett. 1961; 811
- 30 Henrick CA, Willy WE, Baum JW, Baer TA, Garcia BA, Mastre TA, Chang SM. J. Org. Chem. 1975; 40: 1
- 31 Kuchkova KI, Morari AB, Vlad PF. Synthesis 1993; 1221
- 32a Burdon J, McLoughlim VC. R. Tetrahedron 1964; 20: 2163
- 32b Bender ML. J. Am. Chem. Soc. 1953; 75: 5986
- 33 Jenkinson SF, Booth KV, Estevez Reino AM, Horne G, Estevez RJ, Fleet GW. J. Tetrahedron: Asymmetry 2009; 20: 2357
- 34 Maas G, Muller A. Org. Lett. 1999; 1: 219
For reviews on vinylcarbenoids, see:
For selected examples, see:
For reviews on the Horner–Wadsworth–Emmons reaction, see:
For reviews on the Peterson olefination, see:
For reviews on the Still–Gennari reaction, see:
The starting methyl trifluorobutanoate 2f was prepared by a standard procedure.32a It can contain a quantity of the ethyl trifluorobutanoate formed due to base-catalyzed transesterification during Claisen condensation.32b In this case, the ethyl derivative impurity can also be present in the associated vinyl acetate 4f and further reaction products.