Premium
Synthesis of Enantiopure Oxygen‐ and Nitrogen‐Containing Heterocycles by Diastereoselective Ring‐Closing Metathesis Reaction in Perhydro‐1,3‐benzoxazine Derivatives
Author(s) -
GutiérrezLoriente Agustín,
MartínÁlvarez José M.,
Prieto Elena,
Andrés Celia,
Nieto Javier
Publication year - 2019
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201801454
Subject(s) - enantiopure drug , chemistry , diastereomer , ring closing metathesis , salt metathesis reaction , olefin fiber , metathesis , ring (chemistry) , ruthenium , catalysis , enantioselective synthesis , organic chemistry , stereochemistry , polymer , polymerization
Diastereoselective ring‐closing metathesis reactions on chiral trienic perhydro‐1,3‐benzoxazines derived from (−)‐8‐aminomenthol featuring two diastereotopic olefin chains is described. The diastereochemical outcome of the cyclization appeared to be dependent on the length and position of the olefin chains in perhydro‐1,3‐benzoxazine, the degree of substitution of the double bonds and the ruthenium catalyst used. After separation of the diastereomers, and removal of the chiral auxiliary, enantiopure oxygen‐ and nitrogen‐containing heterocycles were obtained.