AI Article Synopsis
- The study focuses on the acid-catalyzed cyclization of alpha-alkyl-substituted (Z)-vinylsilanes that leads to different piperidine and pyrrolidine products.
- Specific reaction conditions allowed for the selective formation of trans-2-alkyl-3-silylpiperidines and other derivatives.
- Notably, variations in the structure of vinylsilane influenced the outcome, with one particular variant yielding only one type of product with high stereoselectivity.
Article Abstract
In the presence of an acid catalyst, alpha-alkyl-substituted (Z)-vinylsilanes 1, bearing a tosylamino group, were smoothly cyclized to trans-2-alkyl-3-silylpiperidines 2 (1,2-silyl-migration products) and (2R*, 1'S*)-2-(1'-silylalkyl)pyrrolidines 3. The elaboration of the reaction conditions enabled the selective preparation of each cyclized product. The acid-catalyzed cyclization of (Z)-vinylsilane 5, whose methylene tether is shorter than that of 1 by one carbon, formed only the 1,2-silyl-migration product 6 with high trans-selectivity. These cyclizations were found to proceed in a stereospecific manner.
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| http://dx.doi.org/10.1002/chir.10150 | DOI Listing |
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