D
K. G. Lalwani, A. Sudalai
Letter
Synlett
Acknowledgment
(12) (a) Cherian, S. K.; Kumar, P. Tetrahedron: Asymmetry 2007, 18,
982. (b) Emmanuvel, L.; Sudalai, A. Tetrahedron Lett. 2008, 49,
5736.
(13) Bilke, J. L.; Moore, S. P.; O’Brien, P.; Gilday, J. Org. Lett. 2009, 11,
1935.
We sincerely thank the CSIR, New Delhi, India and DST-SERB (no.
SB/S1/OC-42/2014) for financial support. K.G.L. thanks the CSIR, New
Delhi, India, for providing a Senior Research Fellowship.
(14) Takahashi, K.; Nakano, H.; Fujita, R. Tetrahedron Lett. 2005, 46,
8927.
Supporting Information
(15) Kumaraswamy, G.; Pitchaiah, A. Tetrahedron 2011, 67, 2536.
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2003, 5, 1685. (b) Zhong, G.; Yu, Y. Org. Lett. 2004, 6, 1637.
(c) Zhong, G. Chem Commun. 2004, 606. (d) Liao, W. W.;
Ibrahem, I.; Cordova, A. Chem. Commun. 2006, 674. (e) Kotkar, S.
P.; Chavan, V. B.; Sudalai, A. Org. Lett. 2007, 9, 1001. (f) Coeffard,
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Supporting information for this article is available online at
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25
Yield: 1.02 g (70%); colorless liquid; [α]D +11.5 (c 1.0, CHCl3);
ee = 93% [chiral HPLC analysis (Chiracel AD-H 250 × 4.6 mm),
n-hexane/i-PrOH, (80:20) 0.5 mL/min, 254 nm), tR = 27.200 min
(minor), tR = 30.607 min (major). IR (CHCl3): 1322, 1463, 1522,
1621, 1719, 3342 cm–1. 1H NMR (200 MHz, CDCl3): δ = 1.41 (s, 9
H), 1.47 (s, 9 H), 2.51 (br s, 1 H), 4.51–4.58 (m, 1 H), 4.72–4.80
(m, 1 H), 5.30 (d, J = 8.1 Hz, 1 H), 6.06 (dd, J = 1.9, 15.7 Hz, 1 H),
6.80 (dd, J = 4.9, 15.7 Hz, 1 H), 7.30–7.37 (m, 5 H). 13C NMR (50
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© Georg Thieme Verlag Stuttgart · New York — Synlett 2016, 27, A–E