Tetrahedron p. 17253 - 17264 (1997)
Update date:2022-09-26
Topics:
Beslin, Pierre
Lelong, Bruno
(Z)-S-alkylic ketene aminothioacetals were prepared from N,N-Dimethyl β-hydroxythioamides 2-8 by deprotonation with LDA (2 eq.) at -78°C followed by S-alkylation with allylic bromide. Rearrangement of these compounds occured easily at room temperature affording major syn N,N-dimethyl β-hydroxy α-allylic thioamides 9-21 with a syn/anti ratio of 80/20 to 98/2. The syn configuration of the major diastereoisomer was confirmed by an univocal synthesis of syn thioamides 9 and 11. The structure assignments were confirmed by empirical 13C NMR rules. The observed induction is well suppported by a proposed transition state model.
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