Z.-Y. Han et al. / Tetrahedron Letters 52 (2011) 5963–5967
5967
5 mol% L3AuMe
O
O
10 mol% 4
+
1a
+
2e
O
O
O
O
toluene, 3 Å MS, 0 °C, 3 d
Ph
1.0 g
N
Ph
N
Ar
anti-3e
Ar
syn-3e
880 mg
93% ee
Ar = 3,4,5-(MeO)3C6H3
LiAlH4, Et2O
84%
.
(1) SO3 Py, Et3N
NNHSO2Ph
O
OH
DMSO, RT, 91%
O
O
(2) PhSO2NHNH2
MgSO4, AcOH
RT, 71%
O
Ph
Ph
HN
HN
Ar
Ar
9
10
Scheme 2. Scale-up of the reaction and identification of the stereochemsitry of syn-3e.
A.-N. R.; Rios, R. Chem. Asian J. 2011, 6, 720; (e) Hewlett, M.; Hupp, C. D.; Tepe, J.
J. Synthesis 2009, 2825.
azlactones to enol ethers by using chiral anion to control the ste-
reochemistry.8,14,15 Further investigations focused on the related
transformations by using the binary catalyst system are underway.
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9182; (b) Liu, X.-Y.; Che, C.-M. Org. Lett. 2009, 11, 4204; (c) Wang, C.; Han, Z.-Y.;
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Acknowledgments
We are grateful for the financial support from NSFC (20732006),
and the Ministry of Health (2009ZX09501-017), MOST (973 Project
2010CB833300), and the Ministry of Education.
Supplementary data
Supplementary data (experimental details and characterization
of new compounds) associated with this article can be found, in the
6. For reviews, see: (a) Akiyama, T. Chem. Rev. 2007, 107, 5744; (b) Terada, M.
Chem. Commun. 2008, 4097; (c) Terada, M. Synthesis 2010, 1929.
7. For a review on gold-g
2-coordination to unsaturated carbon–carbon bonds,
see: Schmidbaur, H.; Schier, A. Organometallics 2010, 29, 2.
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