Abstract
Good neighbors: A chiral auxiliary is used for the first time to control the anomeric selectivity of glycosylation reactions. In this approach, upon treatment with an activator A+, neighboring-group participation pation of an (S)-ethoxycarbonylbenzyl auxiliary at C2 leads to the formation of 1,2-cis glycosides, probably via a transfused ethyloxonium ion intermediate (see scheme).
Original language | English |
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Pages (from-to) | 947-949 |
Number of pages | 3 |
Journal | Angewandte Chemie - International Edition |
Volume | 44 |
Issue number | 6 |
DOIs | |
Publication status | Published - 2 Feb 2005 |
Externally published | Yes |
Keywords
- Anomeric control
- Carbohydrates
- Chiral auxiliaries
- Glycosides
- Glycosylation