Syntheses of Stable Alpha-Silyloxyepoxides and Alpha-Chloroalkyl Silyl Ethers Derivatives of 3,10-Dioxa-5-Azatricyclo[5.2.1.0/2,6]Dec-4-Enes

The Diels-Alder adduct (+/-)-5 of furan to 1-cyanovinyl acetate was converted to (1RS,2RS,6RS,7SR,8SR,10RS)-10-)[(tert-butyl)dimethylsilyl]-oxy}-4-ethoox y (1) and -4-phenyl-3,9,11-trioxa-5-azatetracyclo[5.3.1.0(2,6).0(8,10)]-undec-4-en e (2). These compounds reacted with TiCl4 to afford stable (1RS,2RS,6RS,7SR,8SR,9SR)-9-{[(tert-butyl)dimethylsilyl]oxy)-9-chloro-4- ethoxy-3,10-dioxa-5-azatricyclo[5.2.1.0(2,6)]decan-8-ol (3) and (1RS,2RS,6RS, 7SR,8SR,9SR)-9-{[(tert-butyl)dimethylsilyl}-9-chloro-4-phenyl-3,10-di-ox a-5-azatricyclo[5.2.1.0(2,6]decan-8-ol (4), respectively.


Published in:
Synthetic Communications, 24, 7, 977-988
Year:
1994
ISSN:
0039-7911
Keywords:
Note:
Univ lausanne,chim sect,2 rue barre,ch-1005 lausanne,switzerland.
Laboratories:




 Record created 2005-11-09, last modified 2018-03-17


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