Literature DB >> 27250517

Catalyst-controlled switch of regioselectivity in the asymmetric allylic alkylation of oxazolones with MBHCs.

Gongming Zhu1, Junxian Yang1, Guangjun Bao1, Ming Zhang1, Jing Li1, Yiping Li1, Wangsheng Sun1, Liang Hong2, Rui Wang3.   

Abstract

A catalyst-controlled switch of regioselectivity in asymmetric allylic alkylation of oxazolones with MBHCs was described. The SN2'-SN2' reaction catalysed by a quinine-derived base produced γ-selective secondary allylic oxazolone derivatives, whereas the addition-elimination reaction catalysed by an amino acid-derived bifunctional urea catalyst provided β-selective primary adducts.

Entities:  

Year:  2016        PMID: 27250517     DOI: 10.1039/c6cc03246j

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN: 1359-7345            Impact factor:   6.222


  1 in total

1.  Asymmetric phase-transfer catalysed β-addition of isoxazolidin-5-ones to MBH carbonates.

Authors:  Vito Capaccio; Katharina Zielke; Andreas Eitzinger; Antonio Massa; Laura Palombi; Kirill Faust; Mario Waser
Journal:  Org Chem Front       Date:  2018-10-12       Impact factor: 5.281

  1 in total

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