Paper
The Stereochemistry of Nucleophilic Addition. V. The Reformatsky Reaction of 2-Phenylpropanal with Methyl α-Bromopropionate
Published Oct 1, 1972 · MatsumotoTakashi, FukuiKenji
Bulletin of the Chemical Society of Japan
26
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Abstract
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 LiAlH4 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 LiAlH4 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-cis-pentenoate (VII) and its trans-isomer (VIII), which were then reduced to the corresponding alcohols, IX and X respectively. The cis-hydra...
The Reformatsky reaction of 2-phenylpropanal with methyl -bromopropionate produces diastereomeric methyl 3-hydroxy-2-methyl-4-phenylvalerates, which can be reduced to monotosylates, IVa-IVd, and then to epimeric
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