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

Journal Article


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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.

Authors


  •   Chevis, Philip (external author)
  •   Wangngae, Sirilak (external author)
  •   Thaima, Thanaphat (external author)
  •   Carroll, Anthony (external author)
  •   Willis, Anthony C. (external author)
  •   Pattarawarapan, Mookda (external author)
  •   Pyne, Stephen G.

Publication Date


  • 2019

Citation


  • 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. Chem Comm, 55 (43), 6050-6053.

Scopus Eid


  • 2-s2.0-85066149303

Ro Full-text Url


  • https://ro.uow.edu.au/cgi/viewcontent.cgi?article=1729&context=smhpapers1

Ro Metadata Url


  • http://ro.uow.edu.au/smhpapers1/715

Number Of Pages


  • 3

Start Page


  • 6050

End Page


  • 6053

Volume


  • 55

Issue


  • 43

Place Of Publication


  • United Kingdom

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.

Authors


  •   Chevis, Philip (external author)
  •   Wangngae, Sirilak (external author)
  •   Thaima, Thanaphat (external author)
  •   Carroll, Anthony (external author)
  •   Willis, Anthony C. (external author)
  •   Pattarawarapan, Mookda (external author)
  •   Pyne, Stephen G.

Publication Date


  • 2019

Citation


  • 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. Chem Comm, 55 (43), 6050-6053.

Scopus Eid


  • 2-s2.0-85066149303

Ro Full-text Url


  • https://ro.uow.edu.au/cgi/viewcontent.cgi?article=1729&context=smhpapers1

Ro Metadata Url


  • http://ro.uow.edu.au/smhpapers1/715

Number Of Pages


  • 3

Start Page


  • 6050

End Page


  • 6053

Volume


  • 55

Issue


  • 43

Place Of Publication


  • United Kingdom