Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2018 Oct 12;5(22):3336-3340.
doi: 10.1039/C8QO01057A.

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

Vito Capaccio  1   2 , Katharina Zielke  1 , Andreas Eitzinger  1 , Antonio Massa  2 , Laura Palombi  2 , Kirill Faust  3 , Mario Waser  1
Affiliations

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

Vito Capaccio et al. Org Chem Front. .

Abstract

A novel high yielding, enantio- and diastereoselective protocol for the synthesis of α-allylated highly functionalised β-amino acid derivatives by adding isoxazolidin-5-ones to MBH carbonates under asymmetric phase-transfer catalysis has been developed.

PubMed Disclaimer

Conflict of interest statement

Conflicts of interest There are no conflicts to declare.

Figures

Fig. 1
Fig. 1
Chiral PTCs used in this study.
Scheme 1
Scheme 1
Known reaction of glycine Schiff bases 1 with MBH acetates 3′ and targeted reaction of β-amino acid-based compounds 2 with MBH carbonates 3.
Scheme 2
Scheme 2
Application scope for the asymmetric reaction of β-amino acid-based compounds 2 with MBH carbonates 3 (all reactions were carried out under the conditions shown in entry 19, Table 1; the E : Z ratios were determined by NMR of the crude product mixture; the enantiomeric ratios are given for the major diastereomere and were measured by HPLC using a chiral stationary phase).
Scheme 3
Scheme 3
Heterogenous atmospheric pressure hydrogenation of compound 5a.
See this image and copyright information in PMC

References

    1. For selected reviews: Hashimoto T, Maruoka K. Chem Rev. 2007;107:5656. Ooi T, Maruoka K. Angew Chem, Int Ed. 2007;46:4222. Jew S-s, Park H-g. Chem Commun. 2009:7090. Shirakawa S, Maruoka K. Angew Chem, Int Ed. 2013;52:4312. Novacek J, Waser M. Eur J Org Chem. 2013:637. Herchl R, Waser M. Tetrahedron. 2014;70:1935. Kaneko S, Kumatabara Y, Shirakawa S. Org Biomol Chem. 2016;14:5367. Tan J, Yasuda N. Org Process Res Dev. 2016;20:129. Zong L, Tan C-H. Acc Chem Res. 2017;50:842. Schörgenhumer J, Tiffner M, Waser M. Beilstein J Org Chem. 2017;13:1753.

    1. For reviews on asymmetric phase-transfer catalysis in the synthesis of chiral amino acids: Maruoka K, Ooi T. Chem Rev. 2003;103:3013. O'Donnell MJ. Acc Chem Res. 2004;37:506. Lygo B, Andrews BI. Acc Chem Res. 2004;37:518.

    1. For selected very recent examples: Huo X, Fu J, He X, Chen J, Xie F, Zhang W. Chem Commun. 2018;54:599. De Simone NA, Schettini R, Talotta C, Gaeta C, Izzo I, Della Sala G, Neri P. Eur J Org Chem. 2017:5649. Miguelez J, Miyamura H, Kobayashi S. Adv Synth Catal. 2017;359:2897. Filp U, Pees AL, Taddei C, Pekosak A, Gee AD, Windhorst AD, Poot AJ. Eur J Org Chem. 2017:5154. Wen S, Li X, Lu Y. Asian J Org Chem. 2016;5:1457.

    1. For contributions by our group: Waser M, Gratzer K, HerchI R, Müller N. Org Biomol Chem. 2012;10:251. Gratzer K, Waser M. Synthesis. 2012;44:3661.

    1. Cadart T, Berthonneau C, Levacher V, Perrio S, Briere J-F. Chem – Eur J. 2016;22:15261. - PubMed
    2. Cadart T, Levacher V, Perrio S, Briere J-F. Adv Synth Catal. 2018;360:1499.

LinkOut - more resources