Volume 25, Issue 35
Natural Products
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ChemInform Abstract: Asymmetric Synthesis of N-(Ethoxycarbonyl)-β-methylphenylalanine Esters.

S. FIORAVANTI

S. FIORAVANTI

Dip. Chim., Univ. “La Sapienza”, I-00185 Roma, Italy

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M. A. LORETO

M. A. LORETO

Dip. Chim., Univ. “La Sapienza”, I-00185 Roma, Italy

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L. PELLACANI

L. PELLACANI

Dip. Chim., Univ. “La Sapienza”, I-00185 Roma, Italy

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F. SABBATINI

F. SABBATINI

Dip. Chim., Univ. “La Sapienza”, I-00185 Roma, Italy

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P. A. TARDELLA

P. A. TARDELLA

Dip. Chim., Univ. “La Sapienza”, I-00185 Roma, Italy

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First published: August 30, 1994

Abstract

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ChemInform Abstract

Silyl ketene acetals of (R)-3-phenylbutanoic acid such as (R)-(I), (V) or (VIII) containing different chiral auxiliary moieties are aminated by photolysis with N3-COOEt to give α-amino acid derivatives with 2 stereogenic centers in order to study the relative influence of the chiral auxiliaries with respect to the resident chirality. The diastereoselectivity seems to be affected more by the chirality of the ester moiety than by the resident chirality at the β-C atom.

chemical structure image

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