Synthesis of Oxazolidinones by a Hypervalent Iodine Mediated Cyclization of N‐Allylcarbamates

Mirdyul Das; Arantxa Rodriguez; Pui Kin Tony Lo; Wesley Moran

doi:10.1002/adsc.202001451

Synthesis of Oxazolidinones by a Hypervalent Iodine Mediated Cyclization of N‐Allylcarbamates

Mirdyul Das, Arantxa Rodriguez, Pui Kin Tony Lo, Wesley Moran

Research output: Contribution to journal › Article › peer-review

16 Citations (Scopus)

Abstract

The preparation of oxazolidinones by the hypervalent iodine mediated cyclization of allylcarbamates is described. A versatile range of substrates can be converted into substituted oxazolidinones primed for further transformations. Derivatization of the products at both ends is demonstrated. A preliminary attempt at the enantioselective formation of an oxazolidinone using a chiral iodane is also presented.

Original language	English
Pages (from-to)	1646-1650
Number of pages	5
Journal	Advanced Synthesis and Catalysis
Volume	363
Issue number	6
Early online date	22 Jan 2021
DOIs	https://doi.org/10.1002/adsc.202001451
Publication status	Published - 16 Mar 2021

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title = "Synthesis of Oxazolidinones by a Hypervalent Iodine Mediated Cyclization of N‐Allylcarbamates",

abstract = "The preparation of oxazolidinones by the hypervalent iodine mediated cyclization of allylcarbamates is described. A versatile range of substrates can be converted into substituted oxazolidinones primed for further transformations. Derivatization of the products at both ends is demonstrated. A preliminary attempt at the enantioselective formation of an oxazolidinone using a chiral iodane is also presented.",

keywords = "Iodine, Cyclization, C-O bond formation, Allylic compounds, Addition to alkenes, Hypervalent compounds, C−O bond formation",

author = "Mirdyul Das and Arantxa Rodriguez and Lo, \{Pui Kin Tony\} and Wesley Moran",

note = "Funding Information: We thank Astrastkal Ltd. and the University of Huddersfield for funding. We thank Dr Neil McLay for his NMR expertise. Publisher Copyright: {\textcopyright} 2021 The Authors. Advanced Synthesis \& Catalysis published by Wiley-VCH GmbH Copyright: Copyright 2021 Elsevier B.V., All rights reserved.",

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doi = "10.1002/adsc.202001451",

language = "English",

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journal = "Advanced Synthesis and Catalysis",

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TY - JOUR

T1 - Synthesis of Oxazolidinones by a Hypervalent Iodine Mediated Cyclization of N‐Allylcarbamates

AU - Das, Mirdyul

AU - Rodriguez, Arantxa

AU - Lo, Pui Kin Tony

AU - Moran, Wesley

N1 - Funding Information: We thank Astrastkal Ltd. and the University of Huddersfield for funding. We thank Dr Neil McLay for his NMR expertise. Publisher Copyright: © 2021 The Authors. Advanced Synthesis & Catalysis published by Wiley-VCH GmbH Copyright: Copyright 2021 Elsevier B.V., All rights reserved.

PY - 2021/3/16

Y1 - 2021/3/16

N2 - The preparation of oxazolidinones by the hypervalent iodine mediated cyclization of allylcarbamates is described. A versatile range of substrates can be converted into substituted oxazolidinones primed for further transformations. Derivatization of the products at both ends is demonstrated. A preliminary attempt at the enantioselective formation of an oxazolidinone using a chiral iodane is also presented.

AB - The preparation of oxazolidinones by the hypervalent iodine mediated cyclization of allylcarbamates is described. A versatile range of substrates can be converted into substituted oxazolidinones primed for further transformations. Derivatization of the products at both ends is demonstrated. A preliminary attempt at the enantioselective formation of an oxazolidinone using a chiral iodane is also presented.

KW - Iodine

KW - Cyclization

KW - C-O bond formation

KW - Allylic compounds

KW - Addition to alkenes

KW - Hypervalent compounds

KW - C−O bond formation

UR - https://www.scopus.com/pages/publications/85100455149

U2 - 10.1002/adsc.202001451

DO - 10.1002/adsc.202001451

M3 - Article

SN - 1615-4150

VL - 363

SP - 1646

EP - 1650

JO - Advanced Synthesis and Catalysis

JF - Advanced Synthesis and Catalysis

IS - 6

ER -

Synthesis of Oxazolidinones by a Hypervalent Iodine Mediated Cyclization of N‐Allylcarbamates

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