References
-
1a
Greene TW.
Wuts PGM.
Protective Groups in Organic Synthesis
3rd ed.:
John Wiley and Sons;
New York:
1999.
-
1b
Kocienski PJ.
Protecting Groups
Thieme;
Stuttgart:
1994.
- 2
Nicolaou KC.
Mitchel HJ.
Angew. Chem. Int. Ed.
2001,
40:
1576
-
3a
Fleet GWJ.
Smith PW.
Tetrahedron Lett.
1985,
26:
1469
-
3b
Gerspacher M.
Rapoport H.
J. Org. Chem.
1991,
56:
3700
-
3c
Yadav JS.
Chander MC.
Reddy KK.
Tetrahedron Lett.
1992,
33:
135
-
3d
Manna S.
Viala J.
Yadagiri P.
Falck JR.
Tetrahedron Lett.
1986,
27:
2679
-
3e
Park KH.
Yoon YJ.
Lee SG.
Tetrahedron Lett.
1994,
35:
9737
-
3f
Leblanc Y.
Fitzsimmons BJ.
Adams J.
Perez F.
Rokach J.
J. Org. Chem.
1986,
51:
789
-
3g
Baurle S.
Hoppen S.
Koert U.
Angew. Chem. Int. Ed.
1999,
38:
1263
-
3h
Ichihara A.
Ubukata M.
Sakamura S.
Tetrahedron Lett.
1977,
3473
-
4a
Kim KS.
Song YH.
Lee BH.
Hahn CS.
J. Org. Chem.
1986,
51:
404
-
4b
Iwata M.
Ohrui H.
Bull. Chem. Soc. Jpn.
1981,
54:
2837
-
4c
Vijayasaradhi S.
Singh J.
Aidhen IS.
Synlett
2000,
110
-
4d
Xiao X.
Bai D.
Synlett
2001,
535
-
4e
Swamy NR.
Venkateswarlu Y.
Tetrahedron Lett.
2002,
43:
7549
-
5a
Kozhevnikov IV.
Chem. Rev.
1998,
98:
171
-
5b
Mizuno N.
Misono M.
Chem. Rev.
1998,
98:
199
- 6
Izumi Y.
Hasebe R.
Urabe K.
J. Catal.
1983,
84:
402
- 7
Izumi Y.
Urabe K.
Onaka M.
Zeolite, Clay and Heteropoly Acid in Organic Reactions
Kodansha/VCH;
Tokyo:
1992.
- 8
Kozhevnikova EF.
Derouane EG.
Kozhevnikov IV.
Chem. Commun.
2002,
1178
- 9
Kaur J.
Griffin K.
Harrison B.
Kozhevnikov IV.
J. Catal.
2002,
208:
448
- 10
Firouzabadi H.
Iranpoor N.
Amani K.
Synthesis
2003,
408
- 11
Kishore Kumar GD.
Baskaran S.
Synlett
2004,
1719
12
Typical Experimental Procedure.
(a) Preparation of PMA/SiO
2
Catalyst.
PMA-SiO2 catalyst was prepared following the published procedure.
[11]
(b) Preparation of Terminal Diols.
To a solution of glucose diacetonide (260 mg, 1 mmol) in MeCN (2 mL) were added the 1 mol% PMA/SiO2 (0.01 mmol, based on PMA) followed by 40 µL of H2O, and the reaction mixture was stirred at ambient temperature for 5-7 min. After completion of the reaction as indicated by TLC, the solvent was removed under reduced pressure and the residue was dissolved in THF (2 mL) and filtered. The filtrate was concentrated under reduced pressure and purified by column chromatography (100-200 silica gel mesh) using hexane and EtOAc as solvent system to afford the pure diols. The filtered catalyst was reused without prior drying.
Spectral Data.
Entry b: [α]D +6 (c 1.76, CHCl3). 1H NMR (200 MHz, CDCl3): δ = 7.38 (s, 5 H), 5.75 (d, J = 3.8 Hz, 1 H), 4.64 (dd, J
1,2
= J
2,3
= 3.7 Hz, 1 H), 4.54 (s, 2 H), 3.40-4.00 (m, 6 H), 2.00-2.40 (m, 1 H), 1.48 (s, 3 H), 1.29 (s, 3 H). MS-FAB: m/z = 325.
Entry c: [α]D +2.8 (c 1, MeOH). 1H NMR (200 MHz, CDCl3): δ = 7.78 (d, J = 8.0 Hz, 2 H), 7.38 (d, J = 8.0 Hz, 2 H), 4.83 (d, J = 7.0 Hz, 1 H), 4.15 (d, J = 5.5 Hz, 1 H), 4.05 (d, J = 5.5 Hz, 1 H), 3.90 (d, J = 5.0 Hz, 1 H), 3.52-3.70 (m, 2 H), 2.60 (br s, 1 H), 2.50 (s, 3 H), 2.00 (br s, 1 H), 1.50 (s, 3 H), 1.32 (s, 3 H). MS-FAB: m/z = 389 [M+ + 1].
Entry d: [α]D -16.2 (c 0.4, CHCl3). 1H NMR (200 MHz, CDCl3): δ = 7.35-7.24 (m, 5 H), 6.98-6.82 (m, 1 H), 5.85 (d, J = 15.6 Hz, 1 H), 4.69 (d, J = 11.1 Hz, 1 H), 4.46 (d, J = 11.1 Hz, 1 H), 4.18 (q, J = 7.4 Hz, 2 H), 3.86-3.78 (m, 2 H), 3.50 (dd, J
1,2
= 11.1, J
2,3
= 5.9 Hz, 1 H), 3.35 (dd, J
1,2
= 11.1 Hz, J
2,3
= 5.9 Hz, 1 H), 2.52 (t, J = 6.7 Hz, 2 H), 1.58-1.43 (m, 2 H), 1.28 (t, J = 7.4 Hz, 3 H). MS-FAB: m/z = 331 [M+ + 23], 309 [M+ + 1].