The Stereochemistry of Nucleophilic Addition. V. The Reformatsky Reaction of 2-Phenylpropanal with Methyl α-Bromopropionate
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概要
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The Reformatsky reaction of 2-phenylpropanal (I) with methyl α-bromopropionate gave the diastereomeric methyl 3-hydroxy-2-methyl-4-phenylvalerates, IIa, IIb, IIe, and IId, in a 5 : 24 : 16 : 55 ratio. The configurations of these β-hydroxy esters were assigned by the following experiments. The reduction of IIa–IId with LiAlH<SUB>4</SUB> gave the corresponding diols, IIIa–IIId, which were then converted to the monotosylates, IVa–IVd. The further reduction of IVa or IVc and IVb or IVd with LiAlH<SUB>4</SUB> gave the epimeric 2-methyl-4-phenyl-3-pentanols, V and VI respectively. Since V and VI were also obtained as minor and major products (20 : 80 ratio) of the Grignard reaction of I with isopropylmagnesium iodide, the configurations of the C-3 and C-4 positions in IIa–IId were assigned. The Wittig reaction of I with carbomethoxyethylidenetriphenylphosphorane gave methyl 2-methyl-4-phenyl-2-<I>cis</I>-pentenoate (VII) and its <I>trans</I>-isomer (VIII), which were then reduced to the corresponding alcohols, IX and X respectively. The <I>cis</I>-hydration of IX gave IIIc and IIId, while a similar treatment of X gave IIIa and IIIb. From this experiments, the relative configurations from the C-2 position to the C-3 position in IIa–IId were also assigned. These configurational assignments of IIa–IId were further confirmed by the ozonization of IIa–IId.
- 公益社団法人 日本化学会の論文
著者
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Fukui Kenji
Department Of Chemistry Faculty Of Science Hiroshima University
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Mori Kiyomi
Department of Mechanical Systems Engineering, Faculty of Engineering, Takushoku University, 815-1 Tatemachi, Hachioji, Tokyo 193-0985, Japan
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Matsumoto Takashi
Department of Applied Material Science, Faculty of Integrated Arts and Sciences, University of Tokushima
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Hosoda Yukei
Department of Chemistry, Faculty of Science, Hiroshima University
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