Volume 31, Issue 16
Natural Products
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ChemInform Abstract: Asymmetric Synthesis of α-Amino Acids Based on Carbon Radical Addition to Glyoxylic Oxime Ether.

Hideto Miyabe

Hideto Miyabe

Kobe Pharm. Univ., Higashinada, Kobe 658, Japan

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Chikage Ushiro

Chikage Ushiro

Kobe Pharm. Univ., Higashinada, Kobe 658, Japan

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Masafumi Ueda

Masafumi Ueda

Kobe Pharm. Univ., Higashinada, Kobe 658, Japan

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Kumiko Yamakawa

Kumiko Yamakawa

Kobe Pharm. Univ., Higashinada, Kobe 658, Japan

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Takeaki Naito

Takeaki Naito

Kobe Pharm. Univ., Higashinada, Kobe 658, Japan

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First published: 09 June 2010

Abstract

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ChemInform Abstract

The new carbon radical addition to oxime ethers (I) and (VIII) is studied by varying the reaction conditions such as the presence or absence of Bu3SnH, the type of Lewis acid (e.g. BF3×OEt2 or MgBr2), the type of initiator (Et3B or Et2Zn), the applied solvent, and reaction temperature. A range of enantiomerically pure natural and unnatural α-amino acids may be derived by this method after reductive removal of the benzyloxy and the auxiliary groups.

chemical structure image

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