Journal of Organic Chemistry p. 3600 - 3603 (1984)
Update date:2022-08-05
Topics:
Janssen, Cornelus G. M.
Godefroi, Erik F.
The use of the trimethylsilyl (Me3Si) unit as detachable diastereoselectivity-inducing auxiliary during cationic polycyclization reactions has been examined.Model studies show 2a,b to be easily cyclized to 3a-c in CF3COOH-containing CH2Cl2.Polycyclization of 5a, on treatment with SnCl4 in CH2Cl2, gives a 85:15 ratio of 6a/7a.The same conditions transform 5b into 5percent of 100percent diastereoselectively ortho-cyclized 6b and 46percent of para-cyclized 6c/7c, occurring as a 77:23 epimeric mixture.Desilylation of the cyclized materials, using KO-t-Bu/Me2SO, provides 4a-c and 8a,c.
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