Tetrahedron Letters p. 6561 - 6564 (1998)
Update date:2022-08-03
Topics:
Rae, Alastair
Ker, James
Tabor, Alethea B.
Castro, Jose L.
Parsons, Simon
A direct method for the enantioselective synthesis of propargyl amines has been developed. 4-Substituted (S)-N-Boc-tetrahydro-1,3-oxazines were synthesised and the structure of one analogue determined by X-ray diffraction analysis. Ring-opening using alkynyl Grignard reagents in the presence of BF3.Et2O, followed by removal of the chiral directing group via oxidation and acid-catalysed retro-Michael reaction, gave the desired propargyl amines in good yield.
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