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Organocatalytic Synthesis of Oxazolines and Dihydrooxazines from Allyl‐Amides: Bypassing the Inherent Regioselectivity of the Cyclization
Author(s) -
Theodorou Alexis,
Triandafillidi Ierasia,
Kokotos Christoforos G.
Publication year - 2018
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.201701386
Subject(s) - chemistry , regioselectivity , selectivity , substrate (aquarium) , ring (chemistry) , combinatorial chemistry , organic chemistry , catalysis , oceanography , geology
A selective and efficient methodology for the construction of either oxazolines or dihydrooxazines from the corresponding allyl‐amides is reported. Bypassing the inherent selectivity of the cyclization and depending on the substitution pattern of the substrate, a selective epoxidation‐cyclization was developed leading to either the five‐membered or the six‐membered ring, upon simple and complementary reaction conditions. The cyclization products were obtained in good to excellent yields and high selectivities.