Tetrahedron p. 4627 - 4636 (1989)
Update date:2022-08-04
Topics:
Mooiweer, Hendrik H.
Hiemstra, Henk
Speckamp, W. Nico
The synthesis of a series of χ,δ-unsaturated N-protected α-amino acid methylesters from the coupling of different allylsilanes and glycidyl cation equivalents 6 and 7 is described.Reactions with methoxyglycine derivative 6 are induced with BF3*OEt2; in the case of chloroglycine derivative 7 SnCl4 is used as Lewis acid.Reactions are fully regioselective, but show low stereoselectivity.The conversion of the reaction products into unprotected α-amino acids is described for two cases.
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Doi:10.1039/c5dt01322d
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(2013)Doi:10.3762/bjoc.14.100
(2018)Doi:10.1016/0022-328X(89)85097-1
(1989)Doi:10.1039/c0ob00518e
(2011)Doi:10.1016/j.bmcl.2010.11.064
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