Abstract
Abstract A convenient synthesis of δ,γ-unsaturated amino acids has been developed. After a mixture of ( R )- tert -butanesulfinamide and glyoxylic acid with molecular sieves in CH 2 Cl 2 was stirred for 42 h at room temperature, allylboronic acid pinacol ester was added to the mixture to give ( R )-2-(( R )- tert -butanesulfinamido)pent-4-enoic acid with high diastereoselectivity. The corresponding reaction of ( Z )-crotylboronic acid pinacol ester produced no product; however, that of ( E )-crotylboronic acid pinacol ester produced (2 R, 3 S )-2-(( R )- tert- butylsulfinamido)-3-methylpent-4-enoic acid with excellent diastereoselectivity.
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