A chiral, oxidatively cleavable auxiliary in conjugate additions of lithium amides. Preparation of enantiomerically pure β-amino acid derivatives

Article abstract of DOI:10.1080/00397910008087223

Addition of enantiomerically, pure 4-methoxyphanethyl-substituted lithium amides to α,β-unsaturated esters leads to β-amino acid derivatives 4 - 7 with selectivities > 95: 5. The auxiliary can be cleaved by oxidation with cerium(IV) ammonium nitrate (CAN) and subsequent hydrolysis of the resulting mixture of imines.

Full text of DOI:10.1080/00397910008087223

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Synthetic Communications: An
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A Chiral, Oxidatively
Cleavable Auxiliary in
Conjugate Additions of Lithium
Amides. Preparation of
Enantiomerically Pure β-Amino
Acid Derivatives
Joachim Podlech a
a Institut für Organische Chemie der Universität
Stuttgart, Pfaffenwaldring 55, D-70569, Stuttgart,
Germany
Published online: 04 Dec 2007.
To cite this article: Joachim Podlech (2000) A Chiral, Oxidatively Cleavable Auxiliary
in Conjugate Additions of Lithium Amides. Preparation of Enantiomerically Pure
β-Amino Acid Derivatives, Synthetic Communications: An International Journal
for Rapid Communication of Synthetic Organic Chemistry, 30:10, 1779-1786, DOI:
10.1080/00397910008087223
To link to this article: http://dx.doi.org/10.1080/00397910008087223
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