Premium
Annulation of Oxime‐Ether Tethered Donor–Acceptor Cyclopropanes
Author(s) -
Irwin Lauren C.,
Allen Meredith A.,
Vriesen Matthew R.,
Kerr Michael A.
Publication year - 2020
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.201904521
Subject(s) - annulation , ether , oxime , chemistry , acceptor , stereochemistry , organic chemistry , catalysis , physics , condensed matter physics
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.