Volume 26, Issue 9
Preparative Organic Chemistry
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ChemInform Abstract: Stereoselective Addition of Organoaluminum or Organomanganese Reagents to α-Formyl Amides or α-Methyl-Substituted β-Keto Amides.

M. TANIGUCHI

M. TANIGUCHI

Div. Mater. Chem., Fac. Eng., Kyoto Univ., Sakyo, Kyoto 606-01, Japan

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H. FUJII

H. FUJII

Div. Mater. Chem., Fac. Eng., Kyoto Univ., Sakyo, Kyoto 606-01, Japan

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K. OSHIMA

K. OSHIMA

Div. Mater. Chem., Fac. Eng., Kyoto Univ., Sakyo, Kyoto 606-01, Japan

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K. UTIMOTO

K. UTIMOTO

Div. Mater. Chem., Fac. Eng., Kyoto Univ., Sakyo, Kyoto 606-01, Japan

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First published: February 28, 1995

Abstract

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ChemInform Abstract

Treatment of the α-formyl amides (I) with alkyl- or phenylaluminum dichloride such as (II) provides threo-α-alkyl- substituted β-hydroxy amides of type (III) under high stereocontrol. This method is successfully applied to the selective addition of an alkyl or a phenyl group to α-methyl-substituted . beta.-keto amides or esters of type (V) and (IX) using alkyl- or phenylmanganese chloride, e.g. (VI), or trialkylaluminum such as (X).

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