Issue 43, 2019
From the journal:

Chemical Communications

Highly diastereoselective synthesis of enantioenriched anti-α-allyl-β-fluoroamines†

Philip J. Chevis,‡a   Sirilak Wangngae,‡ab   Thanaphat Thaima,a   Anthony W. Carroll,a   Anthony C. Willis,c   Mookda Pattarawarapanb  and  Stephen G. Pyne ORCID logo *a  

* Corresponding authors

a School of Chemistry and Molecular Biosciences, University of Wollongong, Wollongong, New South Wales, Australia
E-mail: spyne@uow.edu.au

b Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Chiang Mai University, Chiang Mai 50200, Thailand

c Research School of Chemistry, Australian National University, Canberra, ACT 0200, Australia

Abstract

A highly diastereoselective synthesis of anti-α-allyl-β-fluoroamines has been developed involving enantioselective α-fluorination of aldehydes followed by a diastereoselective Petasis allyl borono-Mannich reaction. The products are obtained generally in good overall yields for the two steps and with drs of 97 : 3–99 : 1 and ees of 86–92%. Selected products were converted to 3-, 5- and 6-membered ring heterocycles, the latter two types incorporating an exo-cyclic fluorine.

Graphical abstract: Highly diastereoselective synthesis of enantioenriched anti-α-allyl-β-fluoroamines

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Article information

DOI
https://doi.org/10.1039/C9CC02765C
Article type
Communication
Submitted
10 Apr 2019
Accepted
30 Apr 2019
First published
30 Apr 2019

Chem. Commun., 2019,55, 6050-6053

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Highly diastereoselective synthesis of enantioenriched anti-α-allyl-β-fluoroamines

P. J. Chevis, S. Wangngae, T. Thaima, A. W. Carroll, A. C. Willis, M. Pattarawarapan and S. G. Pyne, Chem. Commun., 2019, 55, 6050 DOI: 10.1039/C9CC02765C

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