Discover Unprotected Amino Aldehydes from Professor Yudin

By: Mark Redlich, Chemfiles Volume 9 Article 3

Professor Andrei Yudin and co-workers have recently described the preparation of bench-stable, unprotected α-amino aldehydes.1These kinetically amphoteric molecules exist as dimers, and due to the strain of the aziridine ring, resist inter- and intramolecular iminium ion formation. Furthermore, the two functionalities remain orthogonal to each other throughout their transformations, allowing for the reaction of the aldehyde without the requirement of an additional protecting group.


α-amino aldehydes

Whereas the reductive amination of protected amino aldehydes has significant limitations due to epimerization or overalkylation, these Yudin amino aldehyde dimers do not suffer from either limitation, due to a negligible concentration of free aldehyde during the reaction. This allows the researcher facile access to a method for the creation of complex polycyclic skeletons2 or peptidomimetic conjugates3 with a high degree of stereocontrol. Nucleophilic additions,4Wittig and related olefination reactions can be carried out with high selectivities and yields. Sigma-Aldrich is pleased to offer these useful Yudin amino aldehydes for your research.

Cascade Polycyclizations

Cascade Polycyclizations

Synthesis of Peptidomimetic Conjugates Without Protecting Groups


Synthesis of Peptidomimetic Conjugates Without Protecting Groups

Unprotected Vinyl Aziridines via Olefination


Unprotected Vinyl Aziridines via Olefination

Unprotected Vicinal 1,2-Amino Alcohols via Allylation with Indium Reagents


Unprotected Vicinal 1,2-Amino Alcohols via Allylation with Indium Reagents

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Materials

     

References

  1. Hili, R.; Yudin, A. K. J. Am. Chem. Soc. 2006, 128, 14772.
  2. Yudin, A. K.; Hili, R. Chem.—Eur. J. 2007, 13, 6538.
  3. Li, X.; Yudin, A. K. J. Am. Chem. Soc. 2007, 129, 14152.
  4. Hili, R.; Yudin, A. K. Angew. Chem., Int. Ed. 2008, 47, 4188.

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