Ring opening of photogenerated azetidinols as a strategy for the synthesis of aminodioxolanes

• Henning Maag,
• Daniel J. Lemcke and
• Johannes M. Wahl

Beilstein J. Org. Chem. 2024, 20, 1671–1676, doi:10.3762/bjoc.20.148

• . Key to the successful development of this two-step process is the identification of a benzhydryl-protecting group, which orchestrates the photochemical Norrish–Yang cyclization and facilitates the subsequent ring opening. Keywords: azetidine; Norrish–Yang cyclization; ring-opening reaction; ring

• by Norrish–Yang cyclization, which employs easily accessible α-aminoacetophenones as starting materials [11][12][13][14][15]. Furthermore, ring-opening reactions of azetidines have been recently achieved using sulfur and oxygen nucleophiles [16][17][18][19][20][21][22][23][24][25]. However, methods

• that target a combination of photochemical ring closure and subsequent functionalization are still underdeveloped [4][5][6][7]. Within this work, we describe our endeavours in identifying a suitable substrate to meet the photochemical requirements of the Norrish–Yang cyclization and allow for

Effects of anion complexation on the photoreactivity of bisureido- and bisthioureido-substituted dibenzobarrelene derivatives

• Heiko Ihmels and
• Jia Luo

Beilstein J. Org. Chem. 2011, 7, 278–289, doi:10.3762/bjoc.7.37

• resulting in regio- or stereoselective product formation. Indeed, this approach has been employed to carry out stereoselective photoreactions, for example [2 + 2] cycloaddition [4], [4 + 4] photocycloaddition [5], Norrish–Yang cyclization [6], and [6π] photocyclization [7]. Asymmetric photoreactions have