RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
Synthesis 2008(17): 2805-2818
DOI: 10.1055/s-2008-1077890
DOI: 10.1055/s-2008-1077890
SPECIALTOPIC
© Georg Thieme Verlag
Stuttgart ˙ New York
N-Heterocyclic Carbene Catalysed Oxygen-to-Carbon Carboxyl Transfer of Indolyl and Benzofuranyl Carbonates
Weitere Informationen
Received
29 March 2008
Publikationsdatum:
06. August 2008 (online)
Publikationsverlauf
Publikationsdatum:
06. August 2008 (online)
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
- 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