Abstract
The formation of a library of diverse macrocycles with different ring sizes from two easily accessible building blocks is presented. Reacting diol precursors with electrophilic reagents lead to 17-membered sulfites and 19-membered malonates in 34–79% yield. Double-reductive amination of dialdehyde analogs of the diol precursors leads to 15-membered amines in yields ranging from 9 to 60%, reflecting large differences in reactivity based on steric environment.
Original language | English |
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Journal | Tetrahedron |
Volume | 66 |
Issue number | 52 |
Pages (from-to) | 9849-9859 |
ISSN | 0040-4020 |
DOIs | |
Publication status | Published - 2010 |
Keywords
- Macrocyclization
- Reductive amination
- Diversity-oriented synthesis
- Cyclic esters