Premium
Organocatalytic Cascade Reactions for the Diversification of Thiopyrano‐Piperidone Fused Rings Utilizing Trienamine Activation
Author(s) -
Mitkari Suhas Balasaheb,
MedinaOrtíz Alberto,
OlivaresRomero José Luis,
Vázquez Miguel A.,
PeñaCabrera Eduardo,
Villegas Gómez Clarisa,
Cruz Cruz David
Publication year - 2021
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202004553
Subject(s) - moiety , cascade , nucleophile , chemistry , ring (chemistry) , cascade reaction , stereochemistry , indole test , chemical space , combinatorial chemistry , catalysis , organic chemistry , drug discovery , biochemistry , chromatography
An aminocatalytic privileged diversity‐oriented synthesis (ApDOS) strategy utilizing trienamine catalysis for the construction of diverse and complex thiopyrans‐piperidone fused rings through a thia‐Diels–Alder/nucleophilic ring‐closing sequence by using dithioamides as activated heterodienophiles is reported. Following this strategy, a super cascade reaction to assemble nine fused rings can be achieved by employing a bis‐dithioamide. Additionally, by linking an indole moiety on the dithioamide, a Pictet–Spengler type reaction can be promoted once the cascade sequence has been achieved, leading to more complex penta‐ hexa‐ and heptacyclic fused ring derivatives in a one‐pot process. This investigation opens new perspectives for the synthesis of a new class of complex and diverse thiopyrans that contribute to populate new relevant regions in the chemical space.