A One-Pot Iodo-Cyclization/Transition Metal-Catalyzed Cross-Coupling Sequence: Synthesis of Substituted Oxazolidin-2-ones from N-Boc-allylamines

Pauline Chaumont-Olive; Janine Cossy

doi:10.1021/acs.orglett.0c01114

A One-Pot Iodo-Cyclization/Transition Metal-Catalyzed Cross-Coupling Sequence: Synthesis of Substituted Oxazolidin-2-ones from N-Boc-allylamines

Org Lett. 2020 May 15;22(10):3870-3874. doi: 10.1021/acs.orglett.0c01114. Epub 2020 Apr 28.

Authors

Pauline Chaumont-Olive¹, Janine Cossy¹

Affiliation

¹ Molecular, Macromolecular Chemistry and Materials, ESPCI Paris, PSL University, CNRS, 75005 Paris, France.

PMID: 32343584
DOI: 10.1021/acs.orglett.0c01114

Abstract

A one-pot iodo-cyclization/transition metal-catalyzed cross-coupling sequence is reported to access various C5-functionalized oxazolidin-2-ones from unsaturated N-Boc-allylamines. Depending on the Grignard reagents used for the cross-coupling, e.g., aryl- or cyclopropylmagnesium bromide, a cobalt or copper catalyst has to be used to obtain the functionalized oxazolidin-2-ones in good yields.