Preparation of N-2-Nitrophenylsulfenyl Imino Peptides and Their Catalyst-Controlled Diastereoselective Indolylation

N-2-Nitrophenylsulfenyl (Nps) imino dipeptides bearing various functional groups were successfully prepared via MnO2-mediated oxidation and then subjected to diastereoselective indolylation. Each diastereomer of the adduct was selectively obtained from the same substrates using the appropriate chiral phosphoric acid catalysts. These transformations would be useful for synthesizing non-canonical amino acid-containing peptides as novel drug candidates.

This is the peer reviewed version of the following article: Inokuma, Tsubasa, Masui, Kana, Fukuhara, Koki, Yamada, Ken-ichi, Chem. Eur. J. 2023, 29, 8, e202203120., which has been published in final form at https://doi.org/10.1002/chem.202203120. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions. This article may not be enhanced, enriched or otherwise transformed into a derivative work, without express permission from Wiley or by statutory rights under applicable legislation. Copyright notices must not be removed, obscured or modified. The article must be linked to Wiley’s version of record on Wiley Online Library and any embedding, framing or otherwise making available the article or pages thereof by third parties from platforms, services and websites other than Wiley Online Library must be prohibited.