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Indium-mediated allylation of carbonyl compounds with an allylic bromide in aqueous media: anomalous syn-diastereoselectivity regardless of allylic bromide geometry

✍ Scribed by Teck-Peng Loh; Zheng Yin; Hong-Yan Song; Kee-Leng Tan

Book ID: 104252843
Publisher: Elsevier Science
Year: 2003
Tongue: French
Weight: 315 KB
Volume: 44
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(02)02773-9

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✦ Synopsis

Anomalous syn-diastereoselectivity of indium-mediated coupling of aldehydes with bromides Z-3b and E-3b is reported. The reaction afforded high syn selectivity regardless of the allylic bromide geometry. Preliminary studies on the enantioselective indium-mediated allylation were attempted and found to give the desired products in moderate yield with high syn selectivity and enantioselectivity.

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