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
Allemann, S.; Yvergnaux, F.; Vogel, P.
1994

Abstract

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.

Details

Title 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
Author(s) Allemann, S. ; Yvergnaux, F. ; Vogel, P.
Published in Synthetic Communications
Volume 24
Issue 7
Pages 977-988
Date 1994
ISSN 0039-7911
Keywords
Note Univ lausanne,chim sect,2 rue barre,ch-1005 lausanne,switzerland.
DOI https://doi.org/10.1080/00397919408020773
Laboratories LGSA
Record Appears in Scientific production and competences > SB - School of Basic Sciences > SB Archives > LGSA - Laboratory of Glycochemistry and Asymmetric Synthesis
Peer-reviewed publications
Work produced at EPFL
Journal Articles
Published
Record creation date 2005-11-09

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