Literature DB >> 23394120

Expedient synthesis of chiral oxazolidinone scaffolds via rhodium-catalyzed asymmetric ring-opening with sodium cyanate.

Gavin Chit Tsui1, Nina M Ninnemann, Akihito Hosotani, Mark Lautens.   

Abstract

A method for synthesizing chiral oxazolidinone scaffolds from readily available oxabicyclic alkenes is described. The reaction utilizes a domino sequence of Rh(I)-catalyzed asymmetric ring-opening (ARO) with sodium cyanate as a novel nucleophile followed by intramolecular cyclization to generate oxazolidinone products in excellent enantioselectivities (trans stereochemistry).

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Year:  2013        PMID: 23394120     DOI: 10.1021/ol4000668

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  2 in total

1.  Gold-catalyzed reaction of oxabicyclic alkenes with electron-deficient terminal alkynes to produce acrylate derivatives.

Authors:  Yin-Wei Sun; Qin Xu; Min Shi
Journal:  Beilstein J Org Chem       Date:  2013-10-01       Impact factor: 2.883

2.  (4S)-4-[(R)-Chloro-(4-nitro-phen-yl)meth-yl]-1,3-oxazolidin-2-one.

Authors:  V Gaumet; C Denis; M Madesclaire; V P Zaitsev
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2013-04-24
  2 in total

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