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

Authors

Philip Chevis, University of WollongongFollow
Sirilak Wangngae, Chiang Mai University, University of Wollongong
Thanaphat Thaima, University of WollongongFollow
Anthony Carroll, University of WollongongFollow
Anthony C. Willis, Australian National University
Mookda Pattarawarapan, Chiang Mai University
Stephen G. Pyne, University of WollongongFollow

RIS ID

135935

Publication Details

Chevis, P. J., Wangngae, S., Thaima, T., Carroll, A. W., Willis, A. C., Pattarawarapan, M. & Pyne, S. G. (2019). Highly diastereoselective synthesis of enantioenriched anti-α-allyl-β-fluoroamines. ChemComm, (43), 6050-6053.

Abstract

A highly diastereoselective synthesis ofanti-a-allyl-b-fluoroamineshas been developed involving enantioselectivea-fluorination ofaldehydes followed by a diastereoselective Petasis allyl borono-Mannich reaction. The products are obtained generally in goodoverall yields for the two steps and with drs of 97 : 3-99 : 1 and eesof 86-92%. Selected products were converted to 3-, 5- and6-membered ring heterocycles, the latter two types incorporatingan exo-cyclic fluorine.