Allenedicarboxylate as a Stereochemically Labile Electrophile for Chiral Organic Base-catalyzed Stereoselective Michael Addition

A highly stereoselective Michael addition of alpha-amino acid-derived 2-benzyloxythiazol-5(4H)-ones to dimethyl allenedicarboxylate was developed by employing P-spiro chiral triamino-iminophosphorane bearing (S)-sec-butyl groups as a catalyst. Theoretical investigation of the transition-state models...

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Bibliographic Details
Published inChemistry letters Vol. 47; no. 4; pp. 594 - 597
Main Authors Uraguchi, Daisuke, Kawai, Yasutaka, Sasaki, Hitoshi, Yamada, Kohei, Ooi, Takashi
Format Journal Article
LanguageEnglish
Published OXFORD Oxford Univ Press 2018
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
Michael addition
BIS(GUANIDINO)IMINOPHOSPHORANE
KETONES
ASYMMETRIC-SYNTHESIS
MANNICH-TYPE REACTION
MECHANISM
Allenedicarboxylate
AMINO-ACIDS
ALPHA
RACEMIZATION
ALLENES
Organocatalysis
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Summary:A highly stereoselective Michael addition of alpha-amino acid-derived 2-benzyloxythiazol-5(4H)-ones to dimethyl allenedicarboxylate was developed by employing P-spiro chiral triamino-iminophosphorane bearing (S)-sec-butyl groups as a catalyst. Theoretical investigation of the transition-state models for the reaction and control experiments suggested the intervention of a dynamic kinetic resolution of the axially chiral allene acceptor. The synthetic utility of this method was demonstrated through the transformation of the stereochemically homogeneous Michael adduct to an alpha-vinylic alpha-amino acid derivative.
Bibliography:KAKEN
ISSN:0366-7022
1348-0715
DOI:10.1246/cl.180031