Organic Letters
ORCID
Letter
3131. (m) Haydl, A. M.; Berthold, D.; Spreider, P. A.; Breit, B. Angew.
Chem., Int. Ed. 2016, 55, 5765; Angew. Chem. 2016, 128, 5859.
n) Beck, T. M.; Breit, B. Org. Lett. 2016, 18, 124. (o) Ganss, S.; Breit,
B. Angew. Chem., Int. Ed. 2016, 55, 9738; Angew. Chem. 2016, 128,
890. (p) Spreider, P. A.; Haydl, A. M.; Heinrich, M.; Breit, B. Angew.
Chem., Int. Ed. 2016, 55, 15569; Angew. Chem. 2016, 128, 15798.
Notes
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9
The authors declare no competing financial interest.
(
(
q) Beck, T. M.; Breit, B. Eur. J. Org. Chem. 2016, 2016, 5839.
r) Haydl, A. M.; Breit, B. Chem. - Eur. J. 2017, 23, 541. (s) Thieme,
ACKNOWLEDGMENTS
■
This work was supported by the DFG and the Fonds der
Chemischen Industrie (PhD fellowship to P.S.). We thank
Solvias, Umicore, BASF, and Wacker for generous gifts of
chemicals. Dr. Manfred Keller and Dr. Daniel Kratzert (both
Albert-Ludwigs-Universitat Freiburg) are acknowledged for
̈
highly qualified NMR and X-ray analysis.
N.; Breit, B. Angew. Chem., Int. Ed. 2017, 56, 1520; Angew. Chem. 2017,
1
1
Chem. - Eur. J. 2017, 23, 6531. (v) Khakyzadeh, V.; Wang, Y.-H.; Breit,
B. Chem. Commun. 2017, 53, 4966. (w) Parveen, S.; Li, C.; Hassan, A.;
Breit, B. Org. Lett. 2017, 19, 2326. (x) Kuang; Parveen, S.; Breit, B.
Angew. Chem., Int. Ed. 2017, 56, 8422; Angew. Chem. 2017, 129, 8542.
29, 1542. (t) Beck, T. M.; Breit, B. Angew. Chem., Int. Ed. 2017, 56,
903; Angew. Chem. 2017, 129, 1929. (u) Schmidt, J.; Li, C.; Breit, B.
(
2
7) (a) Zimmer, R.; Dinesh, C.; Nandanan, E.; Khan, A. F. Chem. Rev.
000, 100, 3067. (b) Kim, I. S.; Krische, M. J. Org. Lett. 2008, 10, 513.
c) Kawamoto, T.; Hirabayashi, S.; Guo, X.; Nishimura, T.; Hayashi,
REFERENCES
■
(
2
1) Quirk, J.; Thornton, M.; Kirkpatrick, P. Nat. Rev. Drug Discovery
003, 2, 769.
(
T. Chem. Commun. 2009, 3528. (d) Moran, J.; Preetz, A.; Mesch, R.
A.; Krische, M. J. Nat. Chem. 2011, 3, 287. (e) Kamijo, S.; Yamamoto,
Y. Tetrahedron Lett. 1999, 40, 1747. (f) Patil, N. T.; Pahadi, N. K.;
Yamamoto, Y. Synthesis 2004, 2004, 2186. (g) Simas, A. B. C.; Plietker,
(
2) Selected reviews concerning 1,3-diols: (a) Oishi, T.; Nakata, T.
Synthesis 1990, 1990, 635. (b) Schneider, C. Angew. Chem., Int. Ed.
998, 37, 1375; Angew. Chem. 1998, 110, 1445. (c) Hoveyda, A. H.;
1
Evans, D. A.; Fu, G. C. Chem. Rev. 1993, 93, 1307. (d) Hoffmann, R.
W. Angew. Chem., Int. Ed. 2000, 39, 2054; Angew. Chem. 2000, 112,
B.; Jak
̈
el, C.; Xie, J.; Trost, B. M. Chem. - Eur. J. 2005, 11, 7075.
(h) Xie, J.; Sieber, J. D.; Trost, B. M. J. Am. Chem. Soc. 2011, 133,
2
(
134.
3) (a) Watanabe, M.; Koike, H.; Ishiba, T.; Okada, T.; Seo, S.; Hirai,
2
9
0611. (i) Kleinbeck, F.; Toste, F. D. J. Am. Chem. Soc. 2009, 131,
178. (j) Zeldin, R. M.; Toste, F. D. Chem. Sci. 2011, 2, 1706. (k) Liu,
K. Bioorg. Med. Chem. 1997, 5, 437. (b) Pfefferkorn, J. A. Art of Drug
Synthesis; Johnson, D. S., Li, J., Eds.; John Wiley & Sons: Hoboken, NJ,
C.; Widenhoefer, R. A. Org. Lett. 2007, 9, 1935. (l) Toups, K. L.; Liu,
G. T.; Widenhoefer, R. A. J. Organomet. Chem. 2009, 694, 571.
2
007, 169. (c) Casar, Z.; Steinbu
̈
cher, M.; Kosmrlj, J. J. Org. Chem.
(8) Selected review concerning the addition of pronucleophiles to
2
010, 75, 6681. (d) Rao, S. V.; Shree, A. J.; Pradhan, B. S.; Vempala,
alkynes: Haydl, A. M.; Breit, B.; Liang, T.; Krische, M. J. Angew. Chem.,
Int. Ed. 2017, 56, 11312; Angew. Chem. 2017, 129, 11466. (a) Trost, B.
M.; Brieden, W. Angew. Chem., Int. Ed. Engl. 1992, 31, 1335; Angew.
Chem. 1992, 104, 1392. (b) Lutete, L. M.; Kadota, I.; Yamamoto, Y. J.
Am. Chem. Soc. 2004, 126, 1622. (c) Cruz, F. A.; Chen, Z.; Kurtoic, S.
I.; Dong, V. M. Chem. Commun. 2016, 52, 5836. (d) Barchuk, A.; Ngai,
M.-Y.; Krische, M. J. J. Am. Chem. Soc. 2007, 129, 8432. (e) Ngai, M.-
Y.; Barchuk, A.; Krische, M. J. J. Am. Chem. Soc. 2007, 129, 12644.
N. Synthesis 2016, 48, 4167. (e) Xiong, F.; Wang, H.; Yan, L.; Han, S.;
Tao, Y.; Wu, Y.; Chen, F. Org. Biomol. Chem. 2016, 14, 1363.
(
4) (a) Liu, G.; Wu, Y. Top. Curr. Chem. 2009, 292, 195. (b) Chen,
M. S.; White, M. C. J. Am. Chem. Soc. 2004, 126, 1346. (c) Liu, G.;
Stahl, S. S. J. Am. Chem. Soc. 2007, 129, 6328. (d) Yin, G.; Wu, Y.; Liu,
G. J. Am. Chem. Soc. 2010, 132, 11978. (e) Takeuchi, R.; Kezuka, S.
Synthesis 2006, 2006, 3349. (f) Helmchen, G.; Dahnz, A.; Dubon, P.;
Schelwies, M.; Weihofen, R. Chem. Commun. 2007, 48, 675. (g) Ye, K.-
Y.; He, H.; Liu, W.-B.; Dai, L.-X.; Helmchen, G.; You, S.-L. J. Am.
Chem. Soc. 2011, 133, 19006. (h) Chen, W.; Hartwig, J. F. J. Am. Chem.
Soc. 2013, 135, 2068. (i) Chen, W.; Hartwig, J. F. J. Am. Chem. Soc.
(
7
(
f) Skucas, E.; Kong, J. R.; Krische, M. J. J. Am. Chem. Soc. 2007, 129,
242. (g) Narsireddy, M.; Yamamoto, Y. J. Org. Chem. 2008, 73, 9698.
h) Patil, N. T.; Wu, H.; Kadota, I.; Yamamoto, Y. J. Org. Chem. 2004,
6
9, 8745. (i) Chen, Q.-A.; Chen, Z.; Dong, V. M. J. Am. Chem. Soc.
2
014, 136, 377. (k) Sandmeier, T.; Krautwald, S.; Zipfel, H. F.;
Carreira, E. M. Angew. Chem., Int. Ed. 2015, 54, 14363; Angew. Chem.
015, 127, 14571. (l) Hamilton, J. Y.; Sarlah, D.; Carreira, E. M. Org.
Synth. 2015, 92, 1.
5) (a) Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395.
b) Trost, B. M.; Crawley, M. L. Chem. Rev. 2003, 103, 2921. (c) Lu,
2
015, 137, 8392.
(9) Liu, Z.; Breit, B. Angew. Chem., Int. Ed. 2016, 55, 8440; Angew.
2
(
(
11) (a) Kabalka, G. W.; Narayana, C.; Reddy, N. K. Tetrahedron
(
(
Lett. 1996, 37, 2181. (b) Hafner, A.; Duthaler, R. O.; Marti, R.; Rihs,
G.; Rothe-Streit, P.; Schwarzenbach, F. J. Am. Chem. Soc. 1992, 114,
Z.; Ma, S. Angew. Chem., Int. Ed. 2008, 47, 258. (d) Vrieze, D. C.;
Hoge, G. S.; Hoerter, P. Z.; Van Haitsma, J. T.; Samas, B. M. Org. Lett.
2
321. (c) Bouzbouz, S.; Cossy, J. Org. Lett. 2000, 2, 501. (d) Paquette,
2
009, 11, 3140. (e) Hayashi, T.; Okada, A.; Suzuka, T.; Kawatsura, M.
L. A.; Mitzel, T. M. Tetrahedron Lett. 1995, 36, 6863. (e) Keck, G. E.;
Murry, J. A. J. Org. Chem. 1991, 56, 6606. (f) Kubota, K.; Leighton, J.
L. Angew. Chem., Int. Ed. 2003, 42, 946; Angew. Chem. 2003, 115, 976.
(12) (a) Mahrwald, R.; Costisella, B. Synthesis 1996, 1996, 1087.
(b) Horiuchi, Y.; Taniguchi, M.; Oshima, K.; Utimoto, K. Tetrahedron
Lett. 1995, 36, 5353. (c) Bodnar, P. M.; Shaw, J. T.; Woerpel, K. A. J.
Org. Chem. 1997, 62, 5674. (d) Mascarenhas, C. M.; Miller, S. P.;
White, P. S.; Morken, J. P. Angew. Chem., Int. Ed. 2001, 40, 601; Angew.
Chem. 2001, 113, 621. (e) Gnanadesikan, V.; Horiuchi, Y.; Ohshima,
T.; Shibasaki, M. J. Am. Chem. Soc. 2004, 126, 7782. (f) Mlynarski, J.;
Mitura, M. Tetrahedron Lett. 2004, 45, 7549. (g) Schneider, C.;
Hansch, M.; Weide, T. Chem. - Eur. J. 2005, 11, 3010.
(13) (a) Evans, D. A.; Chapman, K. T.; Carreira, E. M. J. Am. Chem.
Soc. 1988, 110, 3560. (b) Evans, D. A.; Chapman, K. T. Tetrahedron
Lett. 1986, 27, 5939. (c) Evans, D. A.; Hoveyda, A. H. J. Am. Chem.
Soc. 1990, 112, 6447. (d) Gillespie, K. M.; Munslow, I. J.; Scott, P.
Tetrahedron Lett. 1999, 40, 9371. (e) Fettes, A.; Carreira, E. M. J. Org.
Chem. 2003, 68, 9274.
Org. Lett. 2003, 5, 1713. (f) Evans, P. A.; Leahy, D. K. J. Am. Chem.
Soc. 2002, 124, 7882.
(
6) Selected review concerning the rhodium-catalyzed allylation with
alkynes and allenes: Koschker, P.; Breit, B. Acc. Chem. Res. 2016, 49,
1
1
524. (a) Koschker, P.; Lumbroso, A.; Breit, B. J. Am. Chem. Soc. 2011,
33, 20746. (b) Lumbroso, A.; Koschker, P.; Vautravers, N. R.; Breit,
B. J. Am. Chem. Soc. 2011, 133, 2386. (c) Lumbroso, A.; Abermil, N.;
Breit, B. Chem. Sci. 2012, 3, 789. (d) Cooke, M. L.; Xu, K.; Breit, B.
Angew. Chem., Int. Ed. 2012, 51, 10876−10879; Angew. Chem. 2012,
1
2
24, 11034. (e) Xu, K.; Thieme, N.; Breit, B. Angew. Chem., Int. Ed.
014, 53, 2162; Angew. Chem. 2014, 126, 2194. (f) Xu, K.; Thieme,
N.; Breit, B. Angew. Chem., Int. Ed. 2014, 53, 7268; Angew. Chem. 2014,
26, 7396. (g) Li, C.; Breit, B. J. Am. Chem. Soc. 2014, 136, 862. (h) Li,
C.; Kahny, M.; Breit, B. Angew. Chem., Int. Ed. 2014, 53, 13780; Angew.
1
̈
Chem. 2014, 126, 14000. (i) Pritzius, A. B.; Breit, B. Angew. Chem., Int.
Ed. 2015, 54, 3121−3125; Angew. Chem. 2015, 127, 3164. (j) Pritzius,
A. B.; Breit, B. Angew. Chem., Int. Ed. 2015, 54, 15818; Angew. Chem.
2
2
015, 127, 16044. (k) Haydl, A. M.; Breit, B. Angew. Chem., Int. Ed.
015, 54, 15530−15534; Angew. Chem. 2015, 127, 15750.
(14) (a) Shao, L.; Kawano, H.; Saburi, M.; Uchida, Y. Tetrahedron
1993, 49, 1997. (b) Desroy, N.; Le Roux, R.; Phansavath, P.;
(
̈
l) Koschker, P.; Kahny, M.; Breit, B. J. Am. Chem. Soc. 2015, 137,
D
Org. Lett. XXXX, XXX, XXX−XXX