Organic Letters
Letter
(
c) Zhang, H.; Pu, W.; Xiong, T.; Li, Y.; Zhou, X.; Sun, K.; Liu, Q.;
Scheme 7. Regioselective Deacylation of Adducts 26 and 27
Zhang, Q. Angew. Chem., Int. Ed. 2013, 52, 2529. (d) Hopkins, B. A.;
Wolfe, J. P. Angew. Chem., Int. Ed. 2012, 51, 9886.
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0, 7192. See also: (e) Quiclet-Sire, B.; Zard, S. Z. Heterocycles 2010, 82,
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6, 672. (b) Quiclet-Sire, B.; Zard, S. Z. Chem.Eur. J. 2006, 12, 6002.
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8) (a) Barton, D. H. R.; Jang, D. O.; Jaszberenyi, J. Cs. Tetrahedron
2
(
2
(
proximal acyl group on the nitrogen in enabling the control over
the radical addition.
Lett. 1992, 33, 5709. (b) Boivin, J.; Jrad, R.; Juge, S.; Nguyen, V. T. Org.
Lett. 2003, 5, 1645.
The 1,2-diamino motif is found in numerous biologically active
14
natural and synthetic substances. Biotin is perhaps the most
prominent example, but other representatives include antibiotics
(9) In other words, radical 30 is more stable than radical 19, which in
turn is more stable than the simple secondary radical resulting from the
addition of 19 to an unactivated alkene. It is interesting to note in this
respect that olefin 16 could not be polymerized, in contrast to 17a,
which polymerized readily and furnished after deprotection a polyamine
(
e.g., mitomycins) as well as 1,4-benzodiazepines and various
piperazine-containing drugs. Vicinal diamines are also valuable
for the synthesis of ligands for metals. Despite their
importance, synthetic routes to these structures have remained
relatively limited in variety and scope. The present approach
offers simplicity, flexibility, and modularity. Indeed, many of the
compounds described herein would be tedious to obtain by more
conventional syntheses.
1
5
polymer: Klapper, M.; Hamciuc, C.; Dyllick-Brenzinger, R.; Mu
Angew. Chem., Int. Ed. 2003, 42, 4687.
10) (a) Bertrand, F.; Quiclet-Sire, B.; Zard, S. Z. Angew. Chem., Int. Ed.
Engl. 1999, 38, 1943.
11) Ly, T.-M.; Quiclet-Sire, B.; Sortais, B.; Zard, S. Z. Tetrahedron Lett.
999, 40, 2533.
12) Liard, A.; Quiclet-Sire, B.; Saicic, R. N.; Zard, S. Z. Tetrahedron
̈
llen, K.
16
(
(
1
(
ASSOCIATED CONTENT
Supporting Information
■
Lett. 1997, 38, 1759 The expected cis- stereochemistry in 39 and 40 is
confirmed by the coupling constant of the vicinal hydrogens on the 5-
membered ring (ca 7 Hz).
*
S
Experimental procedures, full spectroscopic data, and copies of
1
13
(13) (a) Osornio, Y. M.; Cruz-Almanza, R.; Jimen
Miranda, L. D. Chem. Commun. 2003, 2316. (b) Reyes-Gutier
Torres-Ochoa, R. O.; Martínez, R.; Miranda, L. D. Org. Biomol. Chem.
009, 7, 1388.
́
ez-Montan
̃
o, V.;
́
rez, P. E.;
2
AUTHOR INFORMATION
■
(14) (a) Saibabu Kotti, S. R. S.; Timmons, C.; Li, G. Chem. Biol. Drug
Des. 2006, 67, 101.
(15) (a) Surry, D. S.; Buchwald, S. L. Chem. Sci. 2010, 1, 13.
(b) Kizirian, J.-C. Chem. Rev. 2008, 108, 140. (c) Hems, W. P.; Groarke,
Notes
M.; Zanotti-Gerosa, A.; Grasa, G. A. Acc. Chem. Res. 2007, 40, 1340.
(16) For reviews, see: (a) De Jong, S.; Nosal, D. G.; Wardrop, D. J.
Tetrahedron 2012, 68, 4067. (b) Lucet, D.; Le Gall, T.; Mioskowski, C.
Angew. Chem., Int. Ed. 1998, 37, 2580. For some recent applications, see:
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
We thank the China Scholarship Council for a grant to one of us
S.H.).
■
(
(c) Bailey, S. J.; Wales, S. M.; Willis, A. C.; Keller, P. A. Org. Lett. 2014,
1
6, 4344. (d) Fujii, S.; Konishi, T.; Matsumoto, Y.; Yamaoka, Y.; Takasu,
K.; Yamada, K. J. Org. Chem. 2014, 79, 8128. (e) Ickes, A. R.; Ensign, S.
C.; Gupta, A. K.; Hull, K. L. J. Am. Chem. Soc. 2014, 136, 11256. (f) Liew,
S. K.; He, Z.; St. Denis, J. D.; Yudin, A. K. J. Org. Chem. 2013, 78, 11637.
(g) Hopkins, B. A.; Wolfe, J. P. Angew. Chem., Int. Ed. 2012, 51, 9886.
DEDICATION
■
This paper is dedicated with respect to the memory of Prof. John
W. Cornforth (University of Sussex).
(h) Olson, D. E.; Su, J. Y.; Roberts, D. A.; Du Bois, J. J. Am. Chem. Soc.
2
014, 136, 13506.
REFERENCES
■
(
1) (a) Chiral Amine Synthesis: Methods, Developments and
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(
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dx.doi.org/10.1021/ol502599r | Org. Lett. 2014, 16, 5386−5389