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. Author manuscript; available in PMC: 2011 Jul 16.
Published in final edited form as: Org Lett. 2010 Jul 16;12(14):3222–3225. doi: 10.1021/ol101144k

Table 2.

Dihydropyran Rearrangements Resulting from Friedel-Crafts Alkylationa

entry substrate product (% yield)b entry substrate product (% yield)b
graphic file with name nihms214548t2.jpg graphic file with name nihms214548t3.jpg 9 graphic file with name nihms214548t4.jpg graphic file with name nihms214548t5.jpg
1 X= OH (10a) 83; (19:23 = 2.8:1) 10 graphic file with name nihms214548t6.jpg graphic file with name nihms214548t7.jpg
2       OTBS (15) 95; (19:23 = 5.5:1; X = OH)
3       OAc (16) 98; (20:24 = 2:1)
4       Br (17) 93; (21)
5       N3 (18) 80; (22:25 = 4.5:1)
graphic file with name nihms214548t8.jpg graphic file with name nihms214548t9.jpg 11 graphic file with name nihms214548t10.jpg graphic file with name nihms214548t11.jpg
6 R = OMe (10b)    26 (97) 12 graphic file with name nihms214548t12.jpg graphic file with name nihms214548t13.jpg
7 R = Me (10c)    27 (81)
8 graphic file with name nihms214548t14.jpg graphic file with name nihms214548t15.jpg
a

Conditions: Sc(OTf)3 (20 mol %), Bu4NPF6 (20 mol %), CH3NO2, 0 °C to rt, 30 min.

b

Isolated yield and ratio.