4
Tetrahedron Letters
9. Yadav, J. S.; Swamy, T.; Reddy, B. V. S. Synlett
(neat): max 3442, 3015, 2915, 1636, 1151, 776 cm-1; 1H
2008, 18, 2773.
NMR (200 MHz, CDCl3): 7.25-7.32 (m, 10H), 5.85 (s,
1H), 4.45-4.65 (m, 4H), 3.95-3.99 (m, 1H), 3.72 (s, 3H),
3.62-3.70 (m, 2H), 3.22 (s, 2H), 2.32-2.40 (m, 2H),
1.95-2.02 (m, 1H), 1.65-1.74 (m, 1H), 1.16 (d, J = 6.0
Hz, 3H); ESI-MS: m/z: 456 (M+18).
10. a) Keck, G. E.; Boden, E. P. Tetrahedron Lett.
1984, 25, 265; b) Williams, D. R.; Klingler, F. D.
Tetrahedron Lett. 1987, 28, 869; c) Annunziata, R.;
Cinquini, M. P. G. J. Org. Chem. 1992, 57, 456.
11. Sharpless, K. B.; Bennani, W. A.; Crispino, G.
A.; Hartung, J.; Jeong, K. S.; Kwong, H. L.; Morikawa,
K.; Wang, Z. M.; Xu, D.; Zhang, X. L. J. Org. Chem.
1992, 57, 2768.
12. Ueno, Y.; Chino, K. J. Chem. Soc. Perkin Trans.
I, 1986, 1351.
13. a) Rama Rao, A. V.; Sharma, G. V. M.; Bhanu,
M. N. Tetrahedron Lett. 1984, 33, 3907; b) Yadav, J. S.;
Reddy, A. S.; Reddy, Ch. S.; Reddy, B. V. S.;
Venkateshwarlu, S.; Anthony, A. Eur. J. Org. Chem.
2011, 696.
14. Spectral data for selected compounds. 2-(4-
20
Methoxybenzyloxymethyl)-(R)-oxirane (8): [α]D
+3.2 (c = 3.5, CHCl3); IR (neat): υmax 2922, 1610, 1245
1
cm-1; H NMR (200 MHz, CDCl3): δ 7.25 (d, J = 8.2
Hz, 2H), 6.81 (d, J = 8.2 Hz, 2H), 4.45 (brs, 2H), 3.81
(s, 3H), 3.69-3.63 (m, 1H), 3.45-3.34 (m, 1H), 3.23-3.18
(m, 1H), 2.76-2.69 (m, 1H), 2.57-2.54 (m, 1H); 13C
NMR (50 MHz, CDCl3): δ 132.2, 130.0, 129.5, 113.5,
74.2, 70.5, 55.3, 50.7, 44.1. ESI-MS: m/z: 194 (M+).
20
(2R,3R)-2-(Benzyloxy)hex-5-en-3-ol (14): [α]D
-
17.58 (c = 3, CHCl3); IR (neat): max 3420, 2927, 1638,
1
1453, 1377, 1091, 748, 698 cm-1; H NMR (200 MHz,
CDCl3): δ 7.31-7.20 (m, 5H), 5.85-5.73 (m, 1H), 5.12-
5.02 (m, 2H), 4.54 (d, J = 6.7 Hz, 2H), 3.74-3.68 (m,
1H), 3.51-3.45 (m, 1H), 2.22 (t, J = 6.5 Hz, 2H), 2.04
(brs, 1H), 1.15 (d, J = 6.0 Hz, 3H); 13C NMR (50 MHz,
CDCl3): δ 138.5, 135.2, 128.5, 128.0, 117.1, 77.4, 74.5,
71.2, 37.8, 15.5; ESI-MS: m/z: 229 (M+Na).
(R)-2-((2R,3R)-2,3-Bis(benzyloxy)butyl)oxirane
(18): [α]D20 +18.4 (c = 3.5, CHCl3); IR (neat): max 3031,
2864, 1733, 1617, 1496, 1453, 1352, 1093, 737, 698 cm-
1
1; H NMR (200 MHz, CDCl3): δ 7.32-7.25 (m, 10H),
4.62-4.52 (m, 4H), 3.74-3.65 (m, 2H), 3.05-2.95 (m,
1H), 2.80-2-65 (m, 1H), 2.52-2.45 (m, 1H), 1.65-1.31
(m, 2H), 1.15 (d, J = 6.0 Hz, 3H); ESI-MS: m/z: 313
(M+1).
(5S,7R,8R)-Methyl
hydroxynon-2-ynoate (5): [α]D +14.28 (c = 2,
7,8-bis(benzyloxy)-5-
20
CHCl3); IR (neat): max 3555, 3031, 2953, 2238, 1714,
1
1435, 1260, 1075, 1027, 947, 771, 753, 700 cm-1; H
NMR (200 MHz, CDCl3): δ 7.35-7.22 (m, 10H), 4.65-
4.50 (m, 4H), 3.95-3.91 (m, 1H), 3.72 (s, 3H), 3.71-3.65
(m, 2H), 2.45 (t, J = 6.0 Hz, 2H), 1.75 (t, J = 6.0 Hz,
2H), 1.16 (d, J = 6.0 Hz, 3H); 13C NMR (50 MHz,
CDCl3): δ 154.5, 138.5, 129.0, 128.1, 86.5, 78.5, 78.0,
77.2, 75.1, 72.5, 71.3, 67.5, 53.1, 36.5, 27.4, 14.7; ESI-
MS: m/z): 397 (M+1).
(E)-Methyl
2-((S)-2-((2R,3R)-2,3-
bis(benzyloxy)butyl)tetrahydro-6-oxopyran-4-
20
ylidene)acetate (2): [α]D +30.0 (c = 0.3, CHCl3); IR