Annulation of Oxime-Ether Tethered Donor-Acceptor Cyclopropanes.

Lauren C IrwinMeredith A AllenMatthew R VriesenMichael A Kerr

Published in: Chemistry (Weinheim an der Bergstrasse, Germany) (2019)

Novel oxime-ether tethered cyclopropanes, when exposed to Yb(OTf)3 and heat, annulate to generate hydropyrrolo-oxazines products that can be taken to their respective pyrrolidines via hydrogenative N-O bond cleavage. The hydropyrrolo-oxazines are generated in a diastereoselective manner isolating the cis or trans product based on the temperature of the reaction. 20 examples of selective cis and trans hydropyrrolo-oxazines were generated in high yields by temperature control.

Keyphrases

energy transfer
ionic liquid
heat stress
dna binding
transcription factor