A Fascination with 1,2-Diacetals
- 13 April 2007
- journal article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 72 (16) , 5943-5959
- https://doi.org/10.1021/jo0703451
Abstract
1,2-Diacetals are readily prepared, rigid structural motifs that provide a wide range of opportunities for applications in natural product assembly. These uses encompass selective 1,2-diol or α-hydroxy acid protection, enantiotopic recognition and desymmetrization methods, chiral memory applications, and reactivity control in oligosaccharide synthesis, as well as functioning as templating components, chiral auxiliaries, and building blocks. 1,2-Diacetals are often more stable and lead to products with enhanced crystallinity compared to their five-ring acetonide counterparts. Many 1,2-diacetals have favorable NMR parameters, which facilitate structural assignment, particularly during asymmetric reaction processes.Keywords
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