Job/Unit: O42336
/KAP1
Date: 11-06-14 18:31:32
Pages: 10
Access to Enantiopure Pyrrolidine Exocyclic Vinylogous Amides
Lett. 2008, 10, 3985–3988; c) A. R. Ranade, G. I. Georg, J.
was concentrated under vacuum and the residue purified by
chromatography over silica gel (diethyl ether/MeOH, 9:1) to yield
a colorless oil (0.31 g, 88%). Rf = 0.61 (diethyl ether/MeOH, 9:1).
[α]2D5 = –14.6 (c = 1, CHCl3). 1H NMR (300 MHz, CDCl3): δ =
9.89 (s, 1 H), 5.06 (s, 1 H), 4.17 (s, 1 H), 4.01 (m, 1 H), 3.73 (dd,
J = 11.5, J = 3.7 Hz, 1 H), 3.53 (dd, J = 11.5, J = 3.7 Hz, 1 H),
2.62 (m, 2 H), 2.20 (t, J = 7.6 Hz, 2 H), 2.05 (m, 1 H), 1.78 (m, 1
H), 1.59 (sext, J = 7.5 Hz, 2 H), 0.91 (t, J = 7.4 Hz, 3 H) ppm. 13C
NMR (75 MHz, CDCl3): δ = 198.4, 167.7, 89.4, 65.1, 62.1, 43.9,
Org. Chem. 2014, 79, 984–992; d) J.-I. Matsuo, S. Sasaki, T.
Hoshikawa, H. Ishibashi, Tetrahedron 2008, 64, 11224–11229;
e) K. Sakamoto, E. Honda, N. Ono, H. Uno, Tetrahedron Lett.
2000, 41, 1819–1823.
[4] a) J. E. Baldwin, J. Chem. Soc., Chem. Commun. 1976, 734–
736; b) K. Gilmore, V. Alabugin, Chem. Rev. 2011, 111, 6513–
6556.
[5] H.-D. Vu, J. Renault, L. Toupet, P. Uriac, N. Gouault, Eur. J.
Org. Chem. 2013, 6677–6686.
[6] S. K. Panday, J. Prasad, D. K. Dikshit, Tetrahedron: Asym-
metry 2009, 20, 1581–1632.
[7] T. Kawabata, W. Muramatsu, T. Nishio, T. Shibata, H. Schedel,
J. Am. Chem. Soc. 2007, 129, 12890–12895.
[8] a) V. S. Kubyshkin, P. K. Mykhailiuk, S. Afonin, A. S. Ulrich,
I. V. Komarov, Org. Lett. 2012, 14, 5254–5257; b) J. Yu, V. Truc,
P. Riebel, E. Hierl, B. Mudryk, Tetrahedron Lett. 2005, 46,
4011–4013.
32.2, 23.4, 19.8, 14.1 ppm. IR (neat): ν = 3293, 2958, 2930, 2871,
˜
1609, 1521, 1300, 1057 cm–1. HRMS (ESI): calcd. for
C10H17NO2Na [M + Na]+ 206.1157; found 206.1160.
Supporting Information (see footnote on the first page of this arti-
1
cle): H and 13C NMR spectra of all compounds; chiral HPLC of
compounds 3a–c, 4a–c, 5a–b, and 7a–c.
[9] a) P. K. Mandal, K. K. Kaluarachchi, D. Ogrin, S. G. Bott,
J. S. McMurray, J. Org. Chem. 2005, 70, 10128–10131; b) V. J.
Colandrea, I. E. Legiec, P. Huo, L. Yan, J. J. Hale, S. G. Mills,
J. Bergstrom, D. Card, G. Chebret, R. Hajdu, C. A. Keohane,
J. A. Milligan, M. J. Rosenbach, G.-J. Shei, S. M. Mandala,
Bioorg. Med. Chem. Lett. 2006, 16, 2905–2908.
[10] CCDC-932590 (for 4a) and -992751 (for 7b) contain the sup-
plementary crystallographic data for this paper. These data can
be obtained free of charge from The Cambridge Crystallo-
graphic Data Center via www.ccdc.cam.ac.uk/data_request/cif.
[11] a) L. Kürti, B. Czako (Ed.), Strategic Applications of Named
Reactions in Organic Synthesis Elsevier, London, 2005, p. 284–
285; b) for a recent review, see: D. A. Engel, G. B. Dudley, Org.
Biomol. Chem. 2009, 7, 4149–4158.
[12] M. J. Niphakis, B. J. Turunen, G. I. Georg, J. Org. Chem. 2010,
75, 6793–6805.
[13] M. N. Pennell, M. G. Unthank, P. Turner, T. D. Sheppard, J.
Org. Chem. 2011, 76, 1479–1482.
[14] L. Banfi, A. Basso, V. Cerulli, G. Guanti, R. Riva, J. Org.
Chem. 2008, 73, 1608–1611.
[15] N. Ikota, Chem. Pharm. Bull. 1992, 40, 1925–1927.
[16] A. A. Malik, R. J. Cormier, C. M. Sharts, Org. Prep. Proced.
Int. 1986, 18, 345–352.
[17] a) M. Roth, P. Dubs, E. Götschi, A. Eschenmoser, Helv. Chim.
Acta 1971, 54, 710–734; b) B. A. D. Neto, A. A. M. Lapis,
A. B. Bernd, D. Russowsky, Tetrahedron 2009, 65, 2484–2496.
[18] a) M. M. Gugelshuk, D. J. Hart, Y. M. Tsaï, J. Org. Chem.
1981, 46, 3671–3675; b) J.-P. Célérier, E. Deloisy, G. Lhommet,
P. Maitte, J. Org. Chem. 1979, 44, 3089–3089.
[19] a) A. Oppedisano, C. Prandi, P. Venturello, A. Deagostino, G.
Goti, D. Scarpi, E. G. Occhiato, J. Org. Chem. 2013, 78, 11007–
11016; b) R. J. Carra, M. T. Epperson, D. Y. Gin, Tetrahedron
2008, 64, 3629–3641; c) C. Herdeis, P. Küpper, S. Plé, Org. Bio-
mol. Chem. 2006, 4, 524–529; d) M. T. Epperson, D. Y. Gin,
Angew. Chem. Int. Ed. 2002, 41, 1778–1780; Angew. Chem.
2002, 114, 1856; e) T. Honda, M. Kimura, Org. Lett. 2000, 2,
3925–3927.
[20] a) L. Felner, K. Shenker, Helv. Chim. Acta 1970, 53, 754–763;
b) T. Kametani, Y. Kigawa, H. Nemoto, M. Ihara, K. Fukum-
oto, J. Chem. Soc. Perkin Trans. 1 1980, 1607–1613; c) A. S.
Howard, R. B. Katz, J. P. Michael, Tetrahedron Lett. 1983, 24,
829–830; d) C. Herdeis, J. Tesler, Eur. J. Org. Chem. 1999, 1407–
1414; e) S. Fréville, P. Delbecq, V. M. Thuy, H. Petit, J.-P.
Célérier, G. Lhommet, Tetrahedron Lett. 2001, 42, 4609–4611;
f) J. P. Michael, C. B. de Koning, D. P. Pienaar, Synlett 2006,
383–386; g) A. G. H. Wee, G.-H. Fan, Org. Lett. 2008, 10,
3869–3872.
Acknowledgments
The authors are deeply grateful to M. Le Roch for technical assist-
ance with the chiral HPLC, Claudia Lalli for manuscript prepara-
tion, P. Jéhan (CRMPO, Université de Rennes 1) for the mass spec-
tra, L. Toupet (IPR, Rennes) and the Ministry of Education and
Training of Vietnam for its financial support.
[1] a) Y. Liu, M. Liu, S. Guo, H. Tu, Y. Zhou, H. Gao, Org. Lett.
2006, 8, 3345–3448; b) K. Stevens, A. J. Tyrrell, S. Skerrat, J.
Robertson, Org. Lett. 2011, 13, 5964–5967; c) N. Gouault, M.
Le Roch, C. Cornée, M. David, P. Uriac, J. Org. Chem. 2009,
74, 5614–5617; d) R. Spina, E. Colacino, B. Gabriele, G. Sa-
lerno, J. Martinez, F. Lamaty, Org. Biomol. Chem. 2012, 10,
9085–9089; e) M. Ostovar, C. M. Marson, Tetrahedron 2013,
69, 6639–6647; f) M. Yoshida, Y. Fujino, T. Doi, Org. Lett.
2011, 13, 4526–4529; g) H. Harkat, A. Blanc, J.-M. Weibel, P.
Pale, J. Org. Chem. 2008, 73, 1620–1623; h) N. Gouault, M.
Le Roch, A. Cheignon, P. Uriac, M. David, Org. Lett. 2011,
13, 4371–4373; i) H. Fuwa, K. Mizunuma, S. Matsukida, M.
Sasaki, Tetrahedron 2011, 67, 4995–5010; j) B. J. Turunen, G. I.
Georg, J. Am. Chem. Soc. 2006, 128, 8702–8703; k) J. Renault,
Z. Qian, P. Uriac, N. Gouault, Tetrahedron Lett. 2011, 52,
2476–2479; l) F. Silva, M. Reiter, R. Mills-Webb, M. Sawicki,
D. Klär, N. Bensel, A. Wagner, V. Gouverneur, J. Org. Chem.
2006, 71, 8390–8394; m) T. Kataoka, H. Kinoshita, S. Kinosh-
ita, T. Iwamura, Tetrahedron Lett. 2002, 43, 7039–7041; n) S.
Dreessen, S. Schabbert, E. Schaumann, Eur. J. Org. Chem.
2001, 245–251; o) K. H. Nguyen, S. Tomasi, M. Le Roch, L.
Toupet, J. Renault, P. Uriac, N. Gouault, J. Org. Chem. 2013,
78, 7809–7815; p) D.-W. Chuang, M. El-Shazly, B. D. Balaji,
Y.-M. Chung, F.-R. Chang, Y.-C. Wu, Eur. J. Org. Chem. 2012,
4533–4540; q) S.-L. Shi, M. Kanai, M. Shibasaki, Angew.
Chem. Int. Ed. 2012, 51, 3932–3935; Angew. Chem. 2012, 124,
3998; r) C. Zhou, A. V. Dubrovsky, R. C. Larock, J. Org. Chem.
2006, 71, 1626–1632; s) M. Schuler, F. Silva, C. Bobbio, A.
Tessier, V. Gouverneur, Angew. Chem. Int. Ed. 2008, 47, 7927–
7930; Angew. Chem. 2008, 120, 8045.
[2] a) M. J. Niphakis, G. I. Georg, J. Org. Chem. 2010, 75, 6019–
6022; b) N. Gouault, M. Le Roch, G. de Campos Pinto, M.
David, Org. Biomol. Chem. 2012, 10, 5541–5546; c) D. Liu,
H. P. Acharya, M. Yu, J. Wang, V. S. C. Yeh, S. Kang, C. Chi-
ruta, S. M. Jachak, D. L. J. Clive, J. Org. Chem. 2009, 74, 7417–
7428; d) T. T. H. Trinh, K. H. Nguyen, P. de Aguiar Amaral,
N. Gouault, Beilstein J. Org. Chem. 2013, 9, 2042–2047; e) M. J.
Niphakis, G. I. Georg, Org. Lett. 2011, 13, 196–199.
[21] W. L. F. Armarego, C. L. L. Chai, Purification of Laboratory
Chemicals, 6th ed., Elsevier, Oxford, UK, 2009.
[3] a) M. J. Niphakis, B. J. Turunen, G. I. Georg, Org. Lett. 2011,
13, 196–199; b) T. N. Grant, C. L. Benson, F. G. West, Org.
Received: March 31, 2014
Published Online:
Eur. J. Org. Chem. 0000, 0–0
© 0000 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
www.eurjoc.org
9