One-Pot Mukaiyama–Mannich Addition Reactions
[10] For representative examples, see: a) C. W. Downey, M. W.
Johnson, D. H. Lawrence, A. S. Fleisher, K. J. Tracy, J. Org.
Chem. 2010, 75, 5351–5354; b) C. W. Downey, A. S. Fleisher,
J. R. Rague, C. L. Safran, M. E. Venable, R. D. Pike, Tetrahe-
dron Lett. 2011, 52, 4756–4759; c) C. Wade Downey, S. E. Co-
vington, D. C. Obenschain, E. Halliday, J. T. Rague, D. N.
Confair, Tetrahedron Lett. 2014, 55, 5213–5215; d) C. W.
Downey, E. N. Maxwell, D. N. Confair, Tetrahedron Lett. 2014,
55, 4959–4961.
Henry Dreyfus Foundation for funding. We are indebted to the
University of California-Riverside for mass spectroscopic data.
[1]
[2]
For recent reviews, see: a) P. Merino, Science of Synthesis (Ed.:
P. W. N. M. van Leeuwen), 2014, 2, 311–331; b) T. Akiyama,
Comp. Org. Synth. 2nd ed. (Eds.: P. Knochel, G. A. Molander)
2014, 2, p. 629–681; c) G. Roman, Eur. J. Med. Chem. 2015,
89, 743–816.
For recent examples, see: a) S. Matsukawa, K. Fukazawa, J.
Kimura, RSC Adv. 2014, 4, 27780–27786; b) E. Lee, T. Ryu, Y.
Park, S. Park, P. H. Lee, Adv. Synth. Catal. 2013, 355, 1585–
1596; c) T. Kano, T. Yurino, D. Asakawa, K. Maruoka, Angew.
Chem. Int. Ed. 2013, 52, 5532–5534; d) B. Ranieri, A. Sartori,
C. Curti, L. Battistini, G. Rassu, G. Pelosi, G. Casiraghi, F.
Zanardi, Org. Lett. 2014, 16, 932–935.
[11] J. E. Huheey, E. A. Keiter, R. L. Keiter, Inorganic Chemistry:
Principles of Structure and Reactivity, 4th ed., Harper Collins,
New York, 1993.
[12] S. Katsuki, M. Ito, Lancet 1966, 2, 530–532.
[13] F. C. Reubi, Ann. N. Y. Acad. Sci. 1966, 139, 433–42.
[14] E. H. Ostergaard, M. P. Magnussen, C. K. Nielsen, E. Ei-
lertsen, H. H. Frey, Arzneim.-Forsch. 1972, 22, 66–72.
[15] N. H. Hauel, H. Nar, H. Priepke, U. Ries, J. M. Stassen, W.
Wienen, H. Nar, H. Priepke, U. Ries, J. M. Stassen, W. Wienen,
J. Med. Chem. 2002, 45, 1757–66.
[3]
[4]
For recent reviews, see: a) N. Mase, C. F. Barbas, III, Compre-
hensive Enantioselective Organocatalysis (Ed.: P. I. Dalko),
2013, 3, p. 793–840; b) N. H. Nguyen, A. B. Hughes, B. E.
Sleebs, Curr. Org. Chem. 2014, 18, 260–289; c) B. Karimi, D.
Enders, E. Jafari, Synthesis 2013, 45, 2769–2812.
For a recent example, see: a) C. Curti, L. Battistini, B. Ranieri,
G. Pelosi, Gl. Rassu, G. Casiraghi, F. Zanardi, J. Org. Chem.
2011, 76, 2248–2252.
[16] The superiority of Et3N vs. iPr2NEt for the deprotonation of
thioesters has been observed in a previous study with nitrone
acceptors; see ref.[8]
[17] For example, N-methylaniline can be silylated with TMSCl and
Et3N in good yield, see: a) C. J. Smith, M. W. S. Tsang, A. B.
Holmes, R. L. Danheiser, J. W. Tester, Org. Biomol. Chem.
2005, 3, 3767–3781; b) C. J. Smith, T. R. Early, A. B. Holmes,
R. E. Shute, Chem. Commun. 2004, 1976–1977.
[5] For recent reviews, see: a) Q. Zhang, X. Liu, X. Feng, Curr.
Org. Synth. 2013, 10, 764–785; b) C. Schneider, M. Sickert, in:
Chiral Amine Synth (Ed.: T. C. Nugent), Wiley, New York,
2010, p. 157–177.
[6] For recent examples, see: a) A. Sartori, L. Dell’Amico, L. Bat-
taistini, C. Curti, S. Rivara, D. Pala, P. S. Kerry, G. Pelosi, G.
Casiraghi, G. Rassu, Org. Biomol. Chem. 2014, 12, 1561–1569;
b) A. Sartori, L. Dell’Amico, C. Curti, L. Battistini, G. Pelosi,
G. Rassu, G. Casiraghi, F. Zanardi, Adv. Synth. Catal. 2011,
353, 3278–3284; c) B. M. Ruff, S. Zhong, M. Nieger, M. Sick-
ert, C. Schneider, S. Brase, Eur. J. Org. Chem. 2011, 6558–6566;
d) S. Dhanasekaran, A. Kayet, A. Suneja, V. Bisai, V. K. Singh,
Org. Lett. 2015, 17, 2780–2783.
[7] For recent examples, see: a) C. R. Jones, G. D. Pantos, A. J.
Morrison, M. D. Smith, Angew. Chem. Int. Ed. 2009, 48, 7391–
7394; Angew. Chem. 2009, 121, 7527; b) Q. Wang, M.
van Gemmeren, B. List, Angew. Chem. Int. Ed. 2014, 53,
13592–13595; c) D. S. Giera, M. Sickert, C. Schneider, Org.
Lett. 2008, 10, 4259–4262; d) F. Abels, C. Lindemann, C.
Schneider, Chem. Eur. J. 2014, 20, 1964–1979.
[8] C. W. Downey, C. M. Dombrowski, E. N. Maxwell, C. L. Saf-
ran, O. A. Akomah, Eur. J. Org. Chem. 2013, 5716–5720.
[9] For Mukaiyama–Mannich additions to nitrones using ester-de-
rived silyl ketene acetals, see: a) C. Qian, L. Wang, Tetrahedron
2000, 56, 7193–7197; b) S.-I. Murahashi, Y. Imada, T. Kawak-
ami, K. Harada, T. Yonemushi, N. Tomita, J. Am. Chem. Soc.
2002, 124, 2888–2889; c) P. Merino, P. Jimenez, T. Tejero, J.
Org. Chem. 2006, 71, 4685–4688; d) A. Diez-Martines, T.
Tehero, P. Merino, Tetrahedron: Asymmetry 2010, 21, 2934–
2943. For computational studies of the mechanism of this reac-
tion type, see: e) A. Milet, Y. Gimbert, A. E. Greene, J. Com-
put. Chem. 2005, 27, 157–162; f) L. R. Domingo, M. Arnó, P.
Merino, T. Tejero, Eur. J. Org. Chem. 2006, 3464–3472.
[18] For a recent example, see: E. B. Rowland, G. B. Rowland, E.
Rivera-Otero, J. C. Antilla, J. Am. Chem. Soc. 2007, 129,
12084–12085.
[19] For a recent example, see ref.[7c]
[20] Identity of major isomer tentatively assigned based on H–H
coupling constants (major: 6.7 Hz, minor: 5.3 Hz).
[21] For a related and highly diastereoselective Ti-mediated aldol
reaction between unactivated esters and O-methyloximes, see:
T. Funatomi, S. Nakazawa, K. Matsumoto, R. Nagase, Y. Tan-
abe, Chem. Commun. 2008, 771–773.
[22] For similar system employing catalytic TIPSOTf, see: S. Ko-
bayashi, H. Kiyohara, M. Yamaguch, J. Am. Chem. Soc. 2011,
133, 708–711.
[23] Secondary amides form relatively unreactive silylimidates un-
der the reaction conditions, see ref.[10b]
[24] For an example of an acylic amide-derived silyl ketene acetal
employed in the Mukaiyama–Mannich reaction, see ref.[7c]
[25] For examples, see ref.[2a,6c,7a,7b,7d] Ethyl ester Mannich products
are frequently prepared under Reformatsky conditions. For re-
cent examples, see: a) S. Sengmany, E. Le Gall, M. Troupel,
Synlett 2008, 1031–1035; b) X. Chen, C. Zhang, H. Wu, X. Yu,
W. Su, J. Cheng, Synthesis 2007, 3233–3239.
[26] a) C. W. Downey, M. W. Johnson, Tetrahedron Lett. 2007, 48,
3559–3562; b) C. W. Downey, M. W. Johnson, K. J. Tracy, J.
Org. Chem. 2008, 73, 3299–3302; see also ref.[8,10c]
[27] a) H. Laurent-Robert, B. Garrigues, J. Dubac, Synlett 2000,
1160–1162; b) Y. Makioka, T. Shindo, Y. Taniguchi, K. Takaki,
Y. Fujiwara, Synthesis 1995, 27, 801–804; c) S. Kobayashi, H.
Ishitani, S. Nagayama, Synthesis 1995, 27, 1195–1202.
[28] A. B. Pangborn, M. A. Giardello, R. H. Grubbs, R. K. Rosen,
F. J. Timmers, Organometallics 1996, 15, 1518–1520.
Received: July 21, 2015
Published Online: October 13, 2015
Eur. J. Org. Chem. 1015, 7287–7291
© 1015 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
www.eurjoc.org
7291