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

Teck Peng Loh; Zheng Yin; Hong Yan Song; Kee Leng Tan

doi:10.1016/S0040-4039(02)02773-9

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

Teck Peng Loh^*, Zheng Yin, Hong Yan Song, Kee Leng Tan

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

35 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	911-914
Number of pages	4
Journal	Tetrahedron Letters
Volume	44
Issue number	5
DOIs	https://doi.org/10.1016/S0040-4039(02)02773-9
Publication status	Published - Jan 27 2003
Externally published	Yes

ASJC Scopus Subject Areas

Biochemistry
Drug Discovery
Organic Chemistry

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abstract = "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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T1 - Indium-mediated allylation of carbonyl compounds with an allylic bromide in aqueous media

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AU - Loh, Teck Peng

AU - Yin, Zheng

AU - Song, Hong Yan

AU - Tan, Kee Leng

PY - 2003/1/27

Y1 - 2003/1/27

N2 - 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.

AB - 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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U2 - 10.1016/S0040-4039(02)02773-9

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ER -

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

Abstract

ASJC Scopus Subject Areas

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