D. F. Taber et al. / Tetrahedron Letters 50 (2009) 2462–2463
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2
2
. Experimental
References and notes
1
2
.
.
Shimojo, M.; Matsumoto, K.; Hatanaka, M. Tetrahedron 2000, 56, 9281.
.1. Procedure for the preparation of 2c
To a solution of commercial allyl magnesium chloride (4.0 mmol)
For the one recorded example of a Grignard reagent (derived from propargyl
bromide) coupling with BOM-Cl, see: Aliev, A. K.; Karaev, S. F.; Gasanov, K. G.
Nauch. Tr. Azerb. In-ta Nefti i Khimii 1979, 59.
3.
Several instances of enolate alkylation with BOM-Cl have been reported. (a)
Kende, A. S.; Chen, J. J. Am. Chem. Soc. 1985, 107, 7184; (b) Lee, B. H.;
Biswas, A.; Miller, M. J. J. Org. Chem. 1986, 51, 106; (c) Brooks, D. W.;
Kellogg, R. P.; Cooper, C. S. J. Org. Chem. 1987, 52, 192; (d) Fujisawa, T.;
Fujimura, A.; Sato, T. Bull. Chem. Soc. Jpn. 1988, 61, 1273; (e) Corey, E. J.;
Yuen, P. W. Tetrahedron Lett. 1989, 30, 5825; (f) Soti, F.; Kajtar-Peredy, M.;
Keresztury, G.; Incze, M.; Kardos-Balogh, Z.; Szantay, C. Tetrahedron 1991,
in THF (8 mL) at 0 °C was added all at once a solution of benzyl chlo-
romethylether (3.8 mmol) in 2 mL of THF. The reaction mixture was
held at 0 °C for 30 min, and then was partitioned between saturated
aqueous NH
Na SO ) and concentrated, and the residue was chromatographed.
Yields are based on benzyl chloromethyl ether charged. 2c: Clear
4
Cl and ether. The combined organic extract was dried
(
2
4
4
7, 271; (g) Mata, E. G.; Thomas, E. J. J. Chem. Soc., Perkin Trans. 1 1995,
1
oil (73% yield), TLC R
NMR (400 MHz, CDCl ) d 2.4 (m, 2H), 4.07 (t, J = 6.8 Hz, 2H), 4.54
s, 2H), 5.04 (d, J = 12.3 Hz, 1H), 5.14 (d, J = 17.2 Hz, 1H), 5.84 (m,
f
= 0.64 (MTBE/petroleum ether 1:10);
H
785; (h) Blakemore, P. R.; Browder, C. C.; Hong, J.; Lincoln, C. M.;
Nagornyy, P. A.; Robarge, L. A.; Wardrop, D. J.; White, J. D. J. Org. Chem.
3
2005, 70, 5449.
(
4
.
.
For the alkylation of the anion derived by deprotonation of a methyl pyridine
with BOM-Cl, see: Leighton, P.; Sanders, J. K. M. J. Chem. Soc., Perkin Trans. 1 1987,
1
3
) d d9 135.2, 128.3,
1
1
H), 7.34 (m, 5H); C NMR (100 MHz, CDCl
27.6, 127.5 u 138.2, 116.3, 72.9, 69.6, 34.2.
3
2385.
5
For the conversion of BOM-Cl into the Grignard reagent and coupling with
an electrophile, see: Crich, D.; Banerjee, A. J. Am. Chem. Soc. 2006, 128,
Acknowledgments
8078.
6
7
8
.
.
.
For a previous preparation of 2c, see: Smith, E. H.; Jeropoulos, S. J. Chem. Soc.,
Chem. Commun. 1986, 1621.
For a previous preparation of 2d, see: Barluenga, J.; Alonso-Cires, L.; Campos, P.;
Asensio, G. Synthesis 1983, 53.
For synthetic applications of 2c, see: (a) Poulter, C. D.; Muehlbacher, M. J. Org.
Chem. 1988, 53, 1026; (b) Legraverend, M.; Boumchita, H.; Zerial, A.; Huel, C.;
Lemaitre, M.; Bisagni, E. J. Med Chem. 1990, 33, 2476; (c) Chan, K.; Ling, Y. H.;
We thank the National Institutes of Health (GM42056) for sup-
port of this work. We thank Dr. John Dykins for mass spectrometric
measurements, supported by the NSF (0541775).
Supplementary data
Loh, T. Chem. Commun. 2007, 939.
1
3C multiplicities were determined with the aid of a JVERT pulse sequence,
9.
General experimental procedures, experimental procedures and
differentiating the signals for methyl and methine carbons as ‘d’ and for
methylene and quaternary carbons as ‘u’.