New Umpolung Catalysts
Chem. 1976, 88, 695–704; Angew. Chem. Int. Ed. Engl. 1976,
15, 639–647; c) H. Stetter, H. Kuhlmann, Org. React. 1991, 40,
407–496; d) K. J. Hawkes, B. F. Yates, Eur. J. Org. Chem. 2008,
5563–5570; e) D. Enders, H. Jianwei, Synlett 2008, 29, 3864–
3868.
Lange, J.-M. Neudörfl, B. Goldfuss, Tetrahedron 2006, 62,
3704–3709; d) F. Soki, J.-M. Neudörfl, B. Goldfuss, J. Or-
ganomet. Chem. 2008, 693, 2139–2146.
[15]
[16]
a) M. Steigelmann, Y. Nisar, F. Röminger, B. Goldfuss, Chem.
Eur. J. 2002, 8, 5211–5218; b) B. Goldfuss, M. Steigelmann, F.
Röminger, Eur. J. Org. Chem. 2000, 1785–1792; c) B. Goldfuss,
M. Steigelmann, Mol. Model. 2000, 6, 166–170; d) B. Goldfuss,
M. Steigelmann, S. I. Khan, K. N. Houk, J. Org. Chem. 2000,
65, 77–82; e) V. Dimitrov, G. Dobrikov, M. Genov, Tetrahe-
dron: Asymmetry 2000, 12, 1323–1329; f) I. Philipova, V. Dimi-
trov, S. Simova, Tetrahedron: Asymmetry 1999, 10, 1381–1391.
a) B. Goldfuss, T. Löschmann, F. Rominger, Chem. Eur. J.
2004, 10, 5422–5431; b) T. Kop-Weiershausen, J. Lex, J.-M.
Neudörfl, B. Goldfuss, Beilstein J. Org. Chem. 2005, 1, 6; c) B.
Goldfuss, T. Löschmann, T. Kop-Weiershausen, J. Neudörfl, F.
Rominger, Beilstein J. Org. Chem. 2006, 2, 7.
For the application of phosphonates as ligands in transition
metal catalysis, see: a) L. Ackermann, Synlett 2007, 507–526;
b) L. Ackermann, A. Althammer, Org. Lett. 2006, 8, 3457–
3460.
S. M. Starling, S. C. Vonwiller, J. N. H. Reek, J. Org. Chem.
1998, 63, 2262–2272.
H. A. Bent, Chem. Rev. 1961, 61, 275–311.
A similar adduct with one of the terpenol-based phosphonates
could not be isolated.
B. Goldfuss, F. Röminger, Tetrahedron 2000, 56, 881–884.
Y. Alpagut, B. Goldfuss, J. Neudörfel, Beilstein J. Org. Chem.
2008, 4, No. 25.
G. M. Sheldrick, Acta Crystallogr. 2008, 64, 112–122; A. L.
Spek, Acta Crystallogr. 2009, 65, 148–155.
M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria,
M. A. Robb, J. R. Cheeseman, J. A. Montgomery Jr., T.
Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar,
J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N.
Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K.
Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y.
Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P.
Hratchian, J. B. Cross, C. Adamo, J. Jaramillo, R. Gomperts,
R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pom-
elli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P.
Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich,
A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D.
Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui,
A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu,
A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J.
Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara,
M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W.
Wong, C. Gonzalez, and J. A. Pople, Gaussian, Inc., Wall-
ingford CT, 2004.
a) R. Ditchfield, W. J. Hehre, J. A. Pople, J. Chem. Phys. 1971,
54, 724; b) V. A. Rassolov, M. A. Ratner, J. A. Pople, P. C.
Redfern, L. A. Curtiss, J. Comput. Chem. 2001, 22, 976.
a) A. D. Becke, J. Chem. Phys. 1993, 98, 5648. For implementa-
tion of the software, see: b) P. J. Stephens, J. Devlin, C. F. Chab-
alowski, M. J. Frisch, J. Phys. Chem. 1994, 98, 11623; c) C.
Lee, W. Yang, R. G. Parr, Phys. Rev. B 1988, 37, 785; d) B.
Miehlich, A. Savin, H. Stoll, H. Preuss, Chem. Phys. Lett. 1989,
157, 200; e) R. Ditchfield, W. J. Hehre, J. A. Pople, J. Chem.
Phys. 1971, 54, 724; f) V. A. Rassolov, M. A. Ratner, J. A. Po-
ple, P. C. Redfern, L. A. Curtiss, J. Comput. Chem. 2001, 22,
976.
[4] For carbenes in acyloin-type couplings, see: a) D. Enders, T.
Balensiefer, Acc. Chem. Res. 2004, 37, 534–541; b) C. Burstein,
F. Glorius, Angew. Chem. 2004, 116, 6331–6334; Angew. Chem.
Int. Ed. 2004, 43, 6205–6208; c) T. Dudding, K. N. Houk, Proc.
Natl. Acad. Sci. USA 2004, 101, 5770–5775; d) D. Enders, O.
Niemeier, T. Balensiefer, Angew. Chem. 2006, 118, 1491–1495;
Angew. Chem. Int. Ed. 2006, 45, 6205–6208; e) A. Berkessel, H.
Gröger, in: Asymmetric Organocatalysis, Wiley-VCH,
Weinheim, Germany, 2005, p. 227; f) H. Takikawa, Y. Hachisu,
J. W. Bode, K. Suzuki, Angew. Chem. 2006, 118, 3572–3574;
Angew. Chem. Int. Ed. 2006, 45, 3492–3494; g) C. Burstein, S.
Tschan, X. Xie, F. Glorius, Synthesis 2006, 2418–2439; h) D.
Enders, O. Niemeier, G. Raabe, Synlett 2006, 2431–2434; i) N.
Marion, S. Díez-González, S. P. Nolan, Angew. Chem. 2007,
119, 3046–3058; Angew. Chem. Int. Ed. 2007, 46, 2988–3000; j)
D. Enders, O. Niemeier, A. Henseler, Chem. Rev. 2007, 107,
5606–5655; k) D. Enders, T. Balensiefer, O. Niemeier, M.
Christmann, in: Enantioselective Organocatalysis (Eds.: P. I.
Dalko), Wiley-VCH, Weinheim, Germany, 2007, 331.
[5] For phosphonates in acyloin-type couplings, Stetter couplings
and Michael additions, see: a) X. Linghu, J. R. Potnick, J. S.
Johnson, J. Am. Chem. Soc. 2004, 126, 3070–3071; b) M. R.
Nahm, X. Linghu, J. R. Potnick, C. M. Yates, P. S. White, J. S.
Johnson, Angew. Chem. 2005, 117, 2429; Angew. Chem. Int. Ed.
2005, 44, 2377; c) M. R. Nahm, J. R. Potnick, P. S. White, J. S.
Johnson, J. Am. Chem. Soc. 2006, 128, 2751–2756; d) D. En-
ders, L. Tedeschi, D. Förster, Synthesis 2006, 9, 1447–1460; e)
L. Tedeschi, D. Enders, Org. Lett. 2001, 3, 3515–3517; f) D.
Enders, A. Saint-Dizier, M. I. Lannou, A. Lenzen, Eur. J. Org.
Chem. 2006, 29–49.
[17]
[18]
[19]
[20]
[21]
[22]
[23]
[24]
[6] A. Lapworth, J. Chem. Soc. 1903, 83, 995–1005.
[7] T. Ugai, R. Tanaka, T. A. Dokawa, J. Pharm. Soc. Jpn. 1943,
63, 296–300; Chem. Abstr. 1951, 45, 5148.
[8] a) R. Breslow, J. Am. Chem. Soc. 1958, 80, 79, 3719–3726; b) R.
Breslow, C. Schmuck, Tetrahedron Lett. 1996, 37, 8241–8242.
[9] For carbenes in Stetter reactions, see: a) M. Christmann, An-
gew. Chem. 2005, 117, 2688–2690; Angew. Chem. Int. Ed. 2005,
44, 2632–2634; b) A. E. Mattson, A. R. Bharadwaj, A. M.
Zuhl, K. A. Scheidt, J. Org. Chem. 2006, 71, 5715–5724; c) J. R.
de Alaniz, T. Rovis, Synlett 2009, 1189–1207.
[10] a) B. Goldfuss, M. Schumacher, J. Mol. Model. 2006, 12, 591–
595; b) B. Goldfuss, M. Schumacher, Tetrahedron 2008, 64,
1648–1653.
[11] For hydrogen bond donor, see: a) Y. Huang, A. K. Unni, A. N.
Thadani, V. H. Rawal, Nature 2003, 424, 146–146; b) K. Mat-
sui, K. Tanaka, A. Horii, S. Takizawa, H. Sasai, Tetrahedron:
Asymmetry 2006, 17, 578–583; c) A. Hasegawa, Y. Naganawa,
M. Fushimi, K. Ishihara, H. Yamamoto, Org. Lett. 2006, 8,
3175–3178.
[12] For Brønsted acid catalysts, see: a) T. Akiyama, Y. Saitoh, H.
Morita, K. Fuchibe, Adv. Synth. Catal. 2005, 347, 1523–1526;
b) D. Uraguchi, M. Terada, J. Am. Chem. Soc. 2004, 126, 5356–
5357; c) M. Ruepening, B. J. Nachtsheim, S. A. Moreth, M.
Bolte, Angew. Chem. 2008, 120, 603–606.
[25]
[26]
[13] For fenchol derivatives, see: a) B. Goldfuss, T. Löschmann, F.
Rominger, Chem. Eur. J. 2001, 7, 2028–2033; B. Goldfuss, T.
Löschmann, F. Rominger, Chem. Eur. J. 2001, 7, 2284; b) F.
Soki, J.-M. Neudörfl, B. Goldfuss, Tetrahedron 2005, 61,
10449–10453.
[14] a) B. Goldfuss, M. Steigelmann, F. Rominger, Angew. Chem.
2000, 112, 4299–4302; b) B. Goldfuss, M. Steigelmann, F.
Rominger, H. Urtel, Chem. Eur. J. 2001, 7, 4456–4464; c) D. A.
[27]
[28]
A. P. Scott, L. Radom, J. Phys. Chem. 1996, 100, 16502.
a) R. Ditchfield, Mol. Phys. 1974, 27, 789; b) W. Wolinski, J. F.
Hinton, P. Pulay, J. Am. Chem. Soc. 1990, 112, 8251.
Received: September 16, 2010
Published Online: November 29, 2010
Eur. J. Org. Chem. 2011, 256–263
© 2011 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
www.eurjoc.org
263