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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 24, 1994 - Issue 22
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Original Articles

Aldol-Type Reaction of α-Halo Ketones with α-Ketocarboxylates Mediated by SmI2 or SmI3: Facile Synthesis of α-Hydroxy-γ-ketocarboxylates

Tsutomu Arime Department of Chemistry, Science University of Tokyo, Kagurazaka, Shinjuku-ku, Tokyo, 162
,
Naoki Kato Department of Chemistry, Science University of Tokyo, Kagurazaka, Shinjuku-ku, Tokyo, 162
,
Fumio Komadate Department of Chemistry, Science University of Tokyo, Kagurazaka, Shinjuku-ku, Tokyo, 162
,
Hiroko Saegusa Department of Chemistry, Science University of Tokyo, Kagurazaka, Shinjuku-ku, Tokyo, 162
&
Nobuo Mori Department of Chemistry, Science University of Tokyo, Kagurazaka, Shinjuku-ku, Tokyo, 162
Pages 3315-3319 | Received 22 Apr 1994, Published online: 23 Sep 2006
 
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Abstract

The title reaction smoothly proceeds at room temperature to give α-hydroxy-γ-keto esters 3 in good yields, probably via a mechanism involving samarium enolates formed in situ from α-halo ketones.

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