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Synthesis 1997; 1997(2): 183-190
DOI: 10.1055/s-1997-1156
DOI: 10.1055/s-1997-1156
paper
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.
Highly Diastereoselective, Nucleophilic Alkenoylation of Enantiopure α-Oxy- and α-Aminoalkanals by Lithiated [1-(p-Toluenesulfonyl)alk-2-enyl] Carbamates. Revision of the Stereochemistry and Application to the Synthesis of a Dihydroxyethylene Dipeptide Isostere
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Publikationsverlauf
Publikationsdatum:
31. Dezember 2000 (online)
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The addition of lithiated [1-(p-toluenesulfonyl)alk-2-enyl] carbamates to α-stereogenic aldehydes proceeds with steric approach control according to the Felkin-Anh model to produce α‘-carbamoyloxy-α,β-enones by carbonyl migration and elimination of p-toluenesulfinate. Conversion of two enones to 1,3-dioxan-2-one 9 and to (2S,3S,4S,5S)-methyl-5-(dibenzylamino)-4-(N,N-diisopropylcarbamoyloxy)-3-hydroxy-2-isopropyl-7-methyloctanoate (16a), respectively, furnished samples suitable for X-ray crystal structure analyses to confirm the stereochemical course of the addition step.
nucleophilic alkenoylation - lithiated allyl carbamates - lithiated allyl sulfones