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Titanium‐Mediated Synthesis of Spirocyclic NH ‐Azetidines from Oxime Ethers
Author(s) -
Behnke Nicole Erin,
Lovato Kaitlyn,
Yousufuddin Muhammed,
Kürti László
Publication year - 2019
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201909151
Subject(s) - oxime , titanium , chemistry , medicinal chemistry , stereochemistry , combinatorial chemistry , organic chemistry
The Ti IV ‐mediated synthesis of spirocyclic NH ‐azetidines from oxime ethers using either an alkyl Grignard reagent or terminal olefin ligand exchange coupling partner is described. Through a proposed Kulinkovich‐type mechanism, a titanacyclopropane intermediate forms and serves as a 1,2‐aliphatic dianion equivalent, inserting into the 1,2‐dielectrophilc oxime ether to ultimately give rise to the desired N‐heterocyclic four‐membered ring. This transformation proceeds in moderate yield to furnish previously unreported and structurally diverse NH ‐azetidines in a single step.