Journal of the American Chemical Society
ARTICLE
D. R.; Edmondson, S. D.; Friedrich, D. Tetrahedron 1994, 50, 4071–
4086. (c) Sodeoka, M.; Sasai, H.; Shibasaki, M. Tetrahedron Lett. 1995,
36, 1067–1070and references therein. (d) Dauben, W. G.; Dinges, J.; Smith,
T. C. J. Org. Chem. 1993, 58, 7635–7637. (e) Ovaska, T. V.; Reisman, S. E.;
Flynn, M. A. Org. Lett. 2001, 3, 115–117and references therein.
(8) Mehta, G.; Singh, V. Chem. Rev. 1999, 99, 881–930.
(9) Bardon, A.; Kamiya, N.; Toyota, M.; Asakawa, Y. Phytochemistry
1999, 51, 281–287.
(22) Trost, B. M.; Chan, V. S.; Yamamoto, D. J. Am. Chem. Soc. 2010,
132, 5186–5192.
(23) (a) Trost, B. M.; Weiss, A. H.; von Wangelin, A. J. J. Am. Chem.
Soc. 2006, 128, 8–9. (b) Trost, B. M.; Weiss, A. H. Org. Lett. 2006,
8, 4461–4464. (c) Trost, B. M.; Weiss, A. H. Angew. Chem., Int. Ed. 2007,
46, 7664–7666. (d) Trost, B. M.; O’Boyle, B. M. J. Am. Chem. Soc. 2008,
130, 16190–16192. (e) Trost, B. M.; O’Boyle, B. M.; Hund, D. J. Am.
Chem. Soc. 2009, 131, 15061–15074.
(10) (a) Feliciano, S.; Barrero, A. F.; Medarde, M.; Miguel del
Corral, J. M.; Aramburu, A. Tetrahedron Lett. 1985, 26, 2369–2372.
(b) Wender, P. A.; Ihle, N. C.; Correia, C. R. D. J. Am. Chem. Soc. 1988,
110, 5904–5906. (c) Limanto, J.; Snapper, M. L. J. Am. Chem. Soc. 2000,
122, 8071–8072. (d) Paquette, L. A.; Jinsung, T.; Arrington, M. P.;
Sadoun, A. H. J. Am. Chem. Soc. 2000, 122, 2742–2748. (e) Krafft, M. E.;
Cheung, Y. Y.; Abboud, K. A. J. Org. Chem. 2001, 66, 7443–7448.
(11) Burke, J. W.; Doskotch, R. W.; Ni, C.-Z.; Clardy, J. J. Am. Chem.
Soc. 1989, 111, 5831–5833. (b) Paquette, L. A.; Borrelly, S. J. Org. Chem.
1995, 60, 6912–6921.
(24) (a) Moore, D.; Pu, L. Org. Lett. 2002, 4, 1855–1857. (b) Gao,
G.; Moore, D.; Xie, R. G.; Pu, L. Org. Lett. 2002, 4, 4143–4146.
(25) (a) Lu, G.; Li, X. S.; Chan, A. S. C. Chem. Commun.
2002, 172–173. (b) Li, X. S.; Lu, G.; Kwok, W. H.; Chan, A. S. C.
J. Am. Chem. Soc. 2002, 124, 12636–12637.
(26) Gao, G.; Xie, R. G.; Pu, L. Proc. Natl. Acad. Sci. U.S.A. 2004,
101, 5417–5420. (d) Gao, G.; Wang, Q.; Yu, X. Q.; Xie, R. G.; Pu, L.
Angew. Chem., Int. Ed. 2006, 45, 122–125.
(27) Yang, F.; Xi, P.; Yang, L.; Lan, J.; Xie, R.; You, J. J. Org. Chem.
2007, 72, 5457–5460.
(12) (a) Jamison, T. F.; Shambayati, S.; Crowe, W. E.; Schreiber,
S. L. J. Am. Chem. Soc. 1994, 116, 5505. (b) Jamison, T. F.; Shambayati,
S.; Crowe, W. E.; Schreiber, S. L. J. Am. Chem. Soc. 1997, 119, 4353–
4363. (c) Paquette, L. A.; Sun, L.-Q.; Friedrich, D.; Savage, P. B. J. Am.
Chem. Soc. 1997, 119, 8438–8450.
(13) (a) Hensens, O. D.; Zink, D.; Williamson, J.; Lotti, V. J.; Chang,
R. S. L.; Goetz, M. A. J. Org. Chem. 1991, 56, 3399–3403. (b) Molander,
G A; Quirmbach, M S; Silva, L F, Jr.; Spencer, K C; Balsells, J. Org. Lett.
2001, 3, 2257–2260.
(28) Du, Y. H.; Turlington, M.; Zhou, X.; Pu, L. Tetrahedron Lett.
2010, 51, 5024–5027.
(29) In analogy to our previous work and others, we assume that the
diynylzinc species is a mixed ethyldiynylzinc intermediate.22,24 For the
complete formation of this intermediate, 16 h was found to be necessary. That
the enantioselectivity is impacted by the stirring time of the first step (see
Table 3, entries 7ꢀ9) implies that the active catalyst is more enantioselective
in the presence of the diynylzinc species than with the unreacted ZnEt2.
(14) Selected reviews: (a) Fletcher, A. J.; Christie, S. D. R. J. Chem.
Soc., Perkin Trans. 1 2000, 1657–1668. (b) Brummond, K. M.; Kent, J. L.
Tetrahedron 2000, 56, 3263–3283. (b) Blanco-Urgoiti, J.; A~norbe, L.;
Pꢀerez-Serrano, L.; Domínguez, G.; Pꢀerez-Castells, J. Chem. Soc. Rev.
2004, 33, 32–42.
(15) Turlington, M.; Yue, Y.; Yu, X.-Q.; Pu, L. J. Org. Chem. 2010,
75, 6941–6952.
(16) Yue, Y.; Turlington, M.; Yu, X.-Q.; Pu, L. J. Org. Chem. 2009,
74, 8681–8689.
(30) Selected examples of highly diastereoselective PK cycloadditions:
(a) Magnus, P.; Exon, R.; Albaugh-Robertson, P. Tetrahedron 1985,
41, 5861–5869. (b) Breczinski, P. M.; Stumpf, A.; Hope, H.; Krafft,
M. E.; Casalnuovo, J. A.; Schore, N. E. Tetrahedron 1999, 55, 6797–
6812. (c) Pagenkopf, B. L.; Belanger, D. B.; O’Mahony, D. J. R.;
Livinghouse, T. Synthesis 2000, 7, 1009–1019. (d) Jiang, B.; Xu, M. Org.
Lett. 2002, 4, 4077–4080. (e) Quintal, M. M.; Closser, K. D.; Shea, K. M.
Org. Lett. 2004, 6, 4949–4952. (f) Areces, P.; Carrasco, E.; Plumet, J.
J. Carb. Chem. 2006, 25, 197–202. (g) Madu, C. E.; Lovely, C. J. Synlett
2007, 13, 2011–2016. (h) Moradov, D.; Quntar, A. A.; Youssef, M.;
Smoum, R.; Rubinstein, A.; Srebnik, M. J. Org. Chem. 2009, 74, 1029–1033.
(i) Farwick, A.; Helmchen, G. Org. Lett. 2010, 12, 1108–1111.
(31) Smit, W. A.; Bukhanyuk, S. M.; Simonyan, S. O.; Shashkov,
A. S.; Struchkov, Y. T.; Yanovskii, A. I.; Caple, R.; Gybin, A. S.; Anderson,
L. G.; Whiteford, J. A. Tetrahedron Lett. 1991, 32, 2105–2108.
(32) Sugihara, T.; Yamada, M.; Yamaguchi, M.; Nishizawa, M.
Synlett 1999, 771–773.
(17) Reviews on enyne metathesis: (a) Diver, S. T.; Giessert, A. J.
Chem. Rev. 2004, 104, 1317–1382. (b) Villar, H.; Frings, M.; Bolm,
C. Chem. Soc. Rev. 2007, 36, 55–66. Selected examples, seven-
membered rings:(c) Kim, S.-H.; Bowden, N.; Grubbs, R. H. J. Am.
Chem. Soc. 1994, 116, 10801–10802. (d) F€urstner, A.; Ackermann, L.;
Gabor, B.; Goddard, R.; Lehmann, C. W.; Mynott, R.; Stelzer, F.; Thiel,
O. R. Chemistry—Eur. J. 2001, 7, 3236–3253. (e) Moreno-Manas, M.;
Pleixats, R.; Santamaria, A. Synlett 2001, 1784–1786. Selected examples,
eight-membered rings:(f) Mori, M.; Kitamura, T.; Sakakibara, N.; Sato,
Y. Org. Lett. 2000, 2, 543–545. (g) Mori, M.; Kitamura, T.; Sato, Y.
Synthesis 2001, 654–664. (h) Boyer, F. D.; Hanna, I.; Ricard, L. Org. Lett.
2001, 3, 3095–3098.
(18) (a) Mukai, C.; Sonobe, H.; Kim, J. S.; Hanoaka, M. J. Org. Chem.
2000, 65, 6654–6659. For formation of seven-membered rings from
allenynes, see:(b) Mukai, C.; Inagaki, F.; Yoshida, T.; Yoshitani, K.;
Hara, Y.; Kitagaki, S. J. Org. Chem. 2005, 70, 7159–7171 and references
therein. (c) Brummond, K. M.; Chen, D.; Davis, M. M. J. Org. Chem.
2008, 73, 5064–5068 and references therein.
(19) (a) Pꢀerez-Serrano, L.; Casarrubios, L.; Domínguez, G.; Pꢀerez-
Castells, J. Chem. Commun. 2001, 2602–2603. (b) Krafft, M. E.; Fu, Z.;
Bo~naga, L. V. R. Tetrahedron Lett. 2001, 42, 1427–1431. (c) Lovely, C. J.;
Seshadri, H.; Wayland, B. R.; Cordes, A. W. Org. Lett. 2001,
3, 2607–2610. (d) Barluenga, J.; Sanz, R.; Fa~nanꢀas, F. J. Chem.—Eur.
J. 1997, 3, 1324–1336.
(20) (a) Frantz, D. E.; F€assler, R.; Tomooka, C. S.; Carreira, E. M.
Acc. Chem. Res. 2000, 33, 373–381. (b) Pu, L. Tetrahedron. 2003,
59, 9873–9886. (c) Cozzi, P. G.; Hilgraf, R.; Zimmermann, N. Eur. J.
Org. Chem. 2004, 4095–4105. (d) Lu, G.; Li, Y.-M.; Li, X.-S.; Chan,
A. S. C. Coord. Chem. Rev. 2005, 249, 1736–1744. (e) Trost, B. M.;
Weiss, A. H. Adv. Synth. Catal. 2009, 351, 963–983.
(33) Tang, Y.; Deng, L.; Zhang, Y.; Dong, G.; Chen, J.; Yang, Z. Org.
Lett. 2005, 7, 593–595.
(34) (a) Hicks, F. A.; Kablaoui, N. M.; Buchwald, S. L. J. Am. Chem.
Soc. 1996, 118, 9450–9451. (b) Hicks, F. A.; Kablaoui, N. M.; Buchwald,
S. L. J. Am. Chem. Soc. 1999, 121, 5881–5898and references therein.
(35) Negishi, E.-I.; Holmes, S. J.; Tour, J. M.; Miller, J. A.;
Cederbaum, F. E.; Swanson, D. R.; Takahashi, T. J. Am. Chem. Soc.
1989, 111, 3336–3346.
(36) (a) Tamao, K.; Kobayashi, K.; Ito, Y. J. Am. Chem. Soc. 1988,
110, 1286–1288. (b) Zhang, M.; Buchwald, S. L. J. Org. Chem. 1996,
61, 4498–4499.
(37) (a) Mukai, C.; Uchiyama, M.; Hanaoka, M. J. Chem. Soc. Chem.
Commun. 1992, 1014–1015. (b) Jeong, N.; Lee, S. L.; Lee, B. Y.; Chung,
Y. K. Tetrahedron Lett. 1993, 34, 4027–4030. (c) Kent, J. L.; Wan, H. H.;
Brummond, K. M. Tetrahedron Lett. 1995, 36, 2407–2410. (d) Adrio, J.;
Rivero, M. R.; Carretero, J. C. Org. Lett. 2005, 7, 431–434. (e) Adrio, J.;
Carretero, J. C. J. Am. Chem. Soc. 2007, 129, 778–779.
(38) (a) Morimoto, T.; Chatani, N.; Fukumoro, Y.; Murai, S. J. Org.
Chem. 1997, 62, 3762–3765. (b) Kondo, T.; Suzuki, N.; Okada, T.;
Mitsudo, T. J. Am. Chem. Soc. 1997, 119, 6187–6188. (c) Kobayashi, T.;
Koga, Y.; Narasaka, K. J. Organomet. Chem. 2001, 624, 73–87.
(21) Reber, S.; Kn€opfel, T. F.; Carreira, E. M. Tetrahedron 2003,
59, 6813–6817.
11793
dx.doi.org/10.1021/ja204289q |J. Am. Chem. Soc. 2011, 133, 11780–11794