Isoxazolidine Explained

Isoxazolidine is the organic compound with the formula (CH₂)₃(NH)O. It is the parent of a family of compounds called Isoxazolidines, which are saturated C₃NO heterocyclic rings where the nitrogen and oxygen occupy adjacent positions (1 and 2). They are the saturated analogues of Isoxazoles, and they are isomeric with oxazolidines, where the N and O are separated by one carbon.^[1]

Isoxazolidines can be produced by the nitrone-olefin (3+2) cycloaddition reaction.

They represent precursors to 1,3-aminoalcohols.^[2] The series Organic Syntheses provides detailed procedures that yield isoxazolidines, e.g., from styrene^[3] and N-phenylmaleimide.^[4] Some isoxazolidines are of medicinal interest.^[5]

References

1. Book: 10.1016/B978-0-08-099406-2.00012-1. Five-Membered Ring Systems. Progress in Heterocyclic Chemistry. 2013. Cordero . Franca M.. Giomi . Donatella. Lascialfari . Luisa. 25. 291–317. 9780080994062.
2. 10.1016/S0040-4020(96)01095-2. Optically active isoxazolidines via asymmetric cycloaddition reactions of nitrones with alkenes: Applications in organic synthesis . 1997 . Frederickson . Martyn . Tetrahedron . 53 . 2 . 403–425 .
3. 10.15227/orgsyn.046.0127. 2,3,5-Triphenylisoxazolidine. Organic Syntheses. 1966. 46. 127. Ingrid . Brüning. Rudolf . Grashey. Hans . Hauck. Rolf . Huisgen. Helmut . Seidl.
4. 10.15227/orgsyn.046.0096. 2-phenyl-3-n-propylisoxazolidine-4,5-cis-dicarboxylic acid n-phenylimide. Organic Syntheses. 1966. 46. 96. Ingrid . Brüning. Rudolf . Grashey. Hans . Hauck. Rolf . Huisgen. Helmut . Seidl.
5. 10.1021/acs.chemrev.6b00543. Isoxazolidine: A Privileged Scaffold for Organic and Medicinal Chemistry. 2016. Berthet . Mathéo. Cheviet . Thomas. Dujardin . Gilles. Parrot . Isabelle. Martinez . Jean. Chemical Reviews. 116. 24. 15235–15283. 27981833.