N-Heterocyclic Carbene
Catalysed Oxygen-to-Carbon Carboxyl Transfer of Indolyl and Benzofuranyl
Carbonates

Jennifer E. Thomson; Andrew F. Kyle; Katherine A. Gallagher; Philip Lenden; Carmen Concellón; Louis C. Morrill; Andrew J. Miller; Caroline Joannesse; Alexandra M. Z. Slawin; Andrew D. Smith

doi:10.1055/s-2008-1077890

SPECIALTOPIC

N-Heterocyclic Carbene Catalysed Oxygen-to-Carbon Carboxyl Transfer of Indolyl and Benzofuranyl Carbonates

Jennifer E. Thomson, Andrew F. Kyle, Katherine A. Gallagher, Philip Lenden, Carmen Concellón, Louis C. Morrill, Andrew J. Miller, Caroline Joannesse, Alexandra M. Z. Slawin, Andrew D. Smith*
EaStCHEM, School of Chemistry, University of St Andrews, North Haugh, St Andrews, KY16 9ST, UK

Abstract

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Abstract

The ability of N-heterocyclic carbenes to promote O-to-C carboxyl transfer on a range of indolyl and benzofuranyl carbonates is examined, and the scope and limitations of this process delineated.

Key words

N-heterocyclic carbene - catalysis - carboxyl transfer

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References

For recent reviews, see:

1a Enders D. Niemeier O. Henseler A. Chem. Rev. 2007, 107: 5606

1b Marion N. Díez-González S. Nolan SP. Angew. Chem. Int. Ed. 2007, 46: 2988

2 Mattson AE. Bharadwaj AR. Zuhl AM. Scheidt KA. J. Org. Chem. 2006, 71: 5715

3a Teles JH. Melder J.-P. Ebel K. Schneider R. Gehrer E. Harder W. Brode S. Enders D. Breuer K. Raabe G. Helv. Chim. Acta 1996, 79: 61

3b Enders D. Breuer K. Teles JH. Helv. Chim. Acta 1996, 79: 1217

3c Enders D. Breuer K. Runsink J. Teles JH. Helv. Chim. Acta 1996, 79: 1899

3d Enders D. Kallfass U. Angew. Chem. Int. Ed. 2002, 41: 1743

3e Kerr MS. Read de Alaniz J. Rovis T. J. Am. Chem. Soc. 2002, 124: 10298

3f Chow KY.-K. Bode JW. J. Am. Chem. Soc. 2004, 126: 8126

3g Reynolds NT. Read de Alaniz J. Rovis T. J. Am. Chem. Soc. 2004, 126: 9518

3h Myers MC. Bharadwaj AR. Milgram BC. Scheidt KA. J. Am. Chem. Soc. 2005, 127: 14675

3i Suzuki Y. Toyota T. Imada F. Sato M. Miyashita A. Chem. Commun. 2003, 1314

For select examples, see:

4a Burstein C. Glorius F. Angew. Chem. Int. Ed. 2004, 43: 6205

4b Sohn SS. Rosen EL. Bode JW. J. Am. Chem. Soc. 2004, 126: 14370

4c Chan A. Scheidt KA. Org. Lett. 2005, 7: 905

For the direct formation of enolates from ketenes, see:

5a Duguet N. Campbell CD. Slawin AMZ. Smith AD. Org. Biomol. Chem. 2008, 6: 1108

5b Zhang Y.-R. He L. Wu X. Shao P.-L. Ye S. Org. Lett. 2008, 10: 277

6 Song JJ. Tan Z. Reeves JT. Gallou F. Yee NK. Senanayake CH. Org. Lett. 2005, 7: 2193

7a Song JJ. Gallou F. Reeves JT. Tan Z. Yee NK. Senanayake CH. J. Org. Chem. 2006, 71: 1273

7b Suzuki Y. Abu Bakar MD. Muramatsu K. Sato M. Tetrahedron 2006, 62: 4227

7c Kano T. Sasaki K. Konishi T. Mii H. Maruoka K. Tetrahedron Lett. 2006, 47: 4615

8a Vora HU. Rovis T. J. Am. Chem. Soc. 2007, 129: 13796

8b Bode JW. Sohn SS. J. Am. Chem. Soc. 2007, 129: 13798

9 Chan A. Scheidt KA. J. Am. Chem. Soc. 2006, 128: 4558

10a Zeitler K. Angew. Chem. Int. Ed. 2005, 44: 7506

10b Reynolds NT. Rovis T. J. Am. Chem. Soc. 2005, 127: 16406

10c Sohn SS. Bode JW. Angew. Chem. Int. Ed. 2006, 45: 6021

11a Sun X. Ye S. Wu J. Eur. J. Org. Chem. 2006, 4787

11b Wu J. Sun X. Ye S. Sun W. Tetrahedron Lett. 2006, 47: 4813

12a Fukada Y. Maeda Y. Kondo K. Aoyama T. Chem. Pharm. Bull. 2006, 54: 397

12b Song JJ. Tan Z. Reeves JT. Yee NK. Senanayake CH. Org. Lett. 2007, 9: 1013

13 For a review, see: Douglas CJ. Overman LE. Proc. Natl. Acad. Sci. U.S.A. 2004, 101: 5363

14a Corey EJ. Angew. Chem. Int. Ed. 2002, 41: 1650

14b Maruoka K. In Catalytic Asymmetric Synthesis 2nd ed.: Ojima I. Wiley-VCH; New York: 2000. p.467-491

14c Kozmin SA. Iwama T. Huang Y. Rawal VH. J. Am. Chem. Soc. 2002, 124: 4628

14d Ryu DH. Corey EJ. J. Am. Chem. Soc. 2003, 125: 6388

14e Evans DA. Wu J. J. Am. Chem. Soc. 2003, 125: 10162

15a O’Donnell MJ. In Catalytic Asymmetric Synthesis 2nd ed.: Ojima I. Wiley-VCH; New York: 2000. p.727-755

15b Trost BM. Van Vranken DL. Chem. Rev. 1996, 96: 395

15c Hodous BL. Fu GC. J. Am. Chem. Soc. 2002, 124: 1578

15d d’Angelo J. Desmaële D. Dumas F. Guingant A. Tetrahedron: Asymmetry 1992, 3: 459

15e Trost BM. Jiang C. J. Am. Chem. Soc. 2001, 123: 12907

15f Austin JF. Kim S.-G. Sinz CJ. Xiao W.-J. MacMillan DWC. Proc. Natl. Acad. Sci. U.S.A. 2004, 101: 5482

15g Bella M. Kobbelgaard S. Jørgensen KA. J. Am. Chem. Soc. 2005, 127: 3670

16a Dounay AB. Overman LE. Chem. Rev. 2003, 103: 2945

16b Donde Y. Overman LE. In Catalytic Asymmetric Synthesis 2nd ed.: Ojima I. Wiley-VCH; New York: 2000. p.675-697

16c Lebsack AD. Link JT. Overman LE. Stearns BA. J. Am. Chem. Soc. 2002, 124: 9008

17a Lachia M. Poriel C. Slawin AMZ. Moody CJ. Chem. Commun. 2007, 286

17b Menozzi C. Dalko PI. Cossy J. Heterocycles 2007, 72: 199

17c Kawasaki T. Shinada M. Kamimura D. Ohzono M. Ogawa A. Chem. Commun. 2006, 420

18a Eder U. Sauer G. Wiechert R. Angew. Chem., Int. Ed. Engl. 1971, 10: 496

18b Hajos ZG. Parrish DR. J. Org. Chem. 1974, 39: 1615

18c Davies SG. Sheppard RL. Smith AD. Thomson JE. Chem. Commun. 2005, 3802

18d Ohshima T. Kagechika K. Adachi M. Sodeoka M. Shibasaki M. J. Am. Chem. Soc. 1996, 118: 7108

18e Wu MH. Hansen KB. Jacobsen EN. Angew. Chem. Int. Ed. 1999, 38: 2012

19 Steglich W. Höfle G. Tetrahedron Lett. 1970, 11: 4727

20 Thomson JE. Rix K. Smith AD. Org. Lett. 2006, 8: 3785

21 Thomson JE. Campbell CD. Concellón C. Duguet N. Rix K. Slawin AMZ. Smith AD. J. Org. Chem. 2008, 73: 2784

For asymmetric versions of this reaction, see:

22a Ruble JC. Fu GC. J. Am. Chem. Soc. 1998, 120: 11532

22b Shaw SA. Aleman P. Vedejs E. J. Am. Chem. Soc. 2003, 125: 13368

22c Shaw SA. Aleman P. Christy J. Kampf JW. Va P. Vedejs E. J. Am. Chem. Soc. 2006, 128: 925

22d Nguyen HY. Butler DCD. Richards CJ. Org. Lett. 2006, 8: 769

22e Seitzberg JG. Dissing C. Søtofte I. Norrby P.-O. Johannsen M. J. Org. Chem. 2005, 70: 8332

22f For the application of this methodology to the preparation of oxindole and benzofuran derivatives, see: Hills ID. Fu GC. Angew. Chem. Int. Ed. 2003, 42: 3921

For the seminal work of Black upon the rearrangement of benzofuranyl carbonates with DMAP, see:

23a Black TH. Arrivo SM. Schumm JS. Knobeloch JM. J. Chem. Soc., Chem. Commun. 1986, 1524

23b Black TH. Arrivo SM. Schumm JS. Knobeloch JM. J. Org. Chem. 1987, 52: 5425

23c Moody CJ. Doyle KJ. Elliott MC. Mowlem TJ. J. Chem. Soc., Perkin Trans. 1 1997, 2413

24 Wiemer et al. have demonstrated extensively the base-catalysed rearrangement of vinyl phosphates to the corresponding β-keto phosphonates; a process driven under thermodynamic control by the formation of a stabilised anion. For an example, see: Calogeropoulou T. Hammond GB. Wiemer DF. J. Org. Chem. 1987, 52: 4185

25 Connolly TJ. Durst T. Can. J. Chem. 1997, 75: 542

26 Takigawa Y. Ito H. Omodera K. Ito M. Taguchi T. Tetrahedron 2004, 60: 1385

27 Shaughnessy KH. Hamann BC. Hartwig JF. J. Org. Chem. 1998, 63: 6546

28 Trost BM. Frederiksen MU. Angew. Chem. Int. Ed. 2005, 44: 308

29 Nishio TJ. Chem. Soc., Perkin Trans. 1 1991, 1717

30 Speeter ME. inventors; U.S. Patent 2759935. ; Chem. Abstr. 1956, 51, 9613

31 Kafka S. Klásek A. Košmrlj J. J. Org. Chem. 2001, 66: 6394

32 Balasubramanian KK. Dhathathreyon KS. Munusamy R. Venkatachalam CS. J. Chem. Soc., Perkin Trans. 2 2001, 1154

33 Huang A. Kodanko JJ. Overman LE. J. Am. Chem. Soc. 2004, 126: 14043

34 Yoneda E. Sugioka T. Hirao K. Zhang S.-W. Takahashi S. J. Chem. Soc., Perkin Trans. 1 1998, 477