Syn Selective Vinylogous Mukaiyama Aldol Reaction Using Z,E-Vinylketene N,O-Acetal with Acetals

Syn Selective Vinylogous Mukaiyama Aldol Reaction Using Z,E-Vinylketene N,O-Acetal with Acetals

Stereoselective vinylogous Mukaiyama aldol reactions using the Z,E-vinylketene silyl N,O-acetal possessing a chiral auxiliary, derived from (E)-3-pentenoic acid and l-valine, have been achieved. The reaction proceeded smoothly to give a syn adduct in high stereoselectivity. Since the products posses...

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Veröffentlicht in:Organic letters 2017-01, Vol.19 (1), p.250-253
Hauptverfasser: Sagawa, Naoya, Moriya, Hiroki, Hosokawa, Seijiro
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creator Sagawa, Naoya
Moriya, Hiroki
Hosokawa, Seijiro
description Stereoselective vinylogous Mukaiyama aldol reactions using the Z,E-vinylketene silyl N,O-acetal possessing a chiral auxiliary, derived from (E)-3-pentenoic acid and l-valine, have been achieved. The reaction proceeded smoothly to give a syn adduct in high stereoselectivity. Since the products possess structures including δ-alkoxy-γ-methyl-α,β-unsaturated imide, this reaction would be applicable to synthesize polyketides in a short procedure.
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title Syn Selective Vinylogous Mukaiyama Aldol Reaction Using Z,E-Vinylketene N,O-Acetal with Acetals
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