One Step Selective Counterion Dependent Formation of Conjugated Chiral N-Sulfinylimines from Aldehydes

Autor:	Jeffrey R, Groch, Nicholas R, Lauta, Jon T, Njardarson
Rok vydání:	2023
Předmět:	Organic Chemistry Physical and Theoretical Chemistry Biochemistry
Zdroj:	Organic Letters. 25:395-399
ISSN:	1523-7052 1523-7060
DOI:	10.1021/acs.orglett.2c04102
Popis:	We report a detailed study on the synthesis and aldehyde vinylogation applications of chiral N-sulfinyl imine phosphonate reagents. Two complementary scalable reagent routes, from trialkyl phosphites and methyl phosphonates, respectively, are presented. This reagent class enables significant streamlining in synthesis of conjugated Ellman imines from aldehydes, which can now be accomplished in a single step compared to a more classic 4-step redox-based approach. Aldehyde vinylogation optimizations have revealed significant counterion effects and unexpected competing reaction challenges that needed to be addressed to achieve high yields.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::cf1eb4267474ffd0b1df47dc67e59980 https://doi.org/10.1021/acs.orglett.2c04102 Zobrazit plný text záznamu