Direct Vinylogous Mannich-Type Reactions via Ring Opening and Rearrangement of Vinyloxiranes
- 8 January 2004
- journal article
- research article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 6 (3) , 345-347
- https://doi.org/10.1021/ol036153j
Abstract
The first synthetic application of 2-methyl-2-vinyloxirane as a masked dienolate has been successfully demonstrated in the direct vinylogous Mannich-type reaction with an α-imino ester as an electrophile. The Mannich adduct was a useful intermediate en route to cis-5-substituted pipecolinic acid ethyl ester under simple hydrogenation conditions.Keywords
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