Tetrahedron p. 4135 - 4146 (1992)
Update date:2022-09-26
Topics:
Beslin, Pierre
Perrio, Stephane
Syn β-hydroxy γ-methyl dithioesters were deprotonated with two equivalents of LDA.A subsequent S-alkylation of the resulting dianions yielded α-hydroxy S-allyl ketene dithioacetals.A single isomer was observed, arising from a selective cis deprotonation.These dithioacetals underwent a rapid and highly diastereoselective thio-Claisen rearrangement at an ambient temperature.Syn-syn α-allyl β-hydroxy γ-methyl dithioesters were mainly formed.The syn-syn/anti-syn ratios ranged from 85 : 15 to 99 : 1.The selectivity observed originates from asymmetric induction with a noteworthy stereoelectronic effect of the hydroxyl group.Configurations were assigned by a spectroscopic method using previously reported 13C NMR rules and then confirmed by a syn-syn diastereoselective aldol reaction.This novel and efficient method for the creation of frameworks with three contiguous stereogenic centres, involves two diastereoselective steps: an aldol reaction followed by a thio-Claisen rearrangement.
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