Synthesis of chiral helical 1,3-oxazines.
A series of novel 1,3-oxazines were prepared to construct a helical framework. The 1,3-oxazine attached to the phenanthrene unit showed a small bite angle θ (∼12°), while the units attached to [4]helicene showed a larger θ (∼35°) and exhibited helical isomers at ambient conditions. The diastereomers of the third type of helicene-like bis-oxazine attached to binaphthyl were easily separable and showed good thermal stability. All four diastereomers of bis-helicene were synthesized, and their absolute configuration was established.
Department of Chemistry, Faculty of Science, M.S. University of Baroda, Vadodara 390 002, India.
Harish R
HR
Talele
Sibaprasad
S
Sahoo
Ashutosh V
AV
Bedekar
D002942:Circular Dichroism; D008958:Models, Molecular; D015394:Molecular Structure; D010078:Oxazines / Q000138:chemical synthesis*; D013237:Stereoisomerism
D010078:Oxazines