Indium - Copper-mediated barbier - Grignard-type alkylation reaction of imines in aqueous media

Zhi Liang Shen; Teck Peng Loh

doi:10.1021/ol702263b

Indium - Copper-mediated barbier - Grignard-type alkylation reaction of imines in aqueous media

Zhi Liang Shen, Teck Peng Loh

Nanyang Technological University

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

52 Scopus citations

Abstract

An efficient system of In/Cul/InCl₃ was developed for Barbier-Grignard-type alkylation reactions of simple imines, using a one-pot condensation of various aldehydes, amines (including aliphatic and chiral version), and alkyl iodides in water or aqueous media. The reactions proceeded efficiently at room temperature to give the desired products in moderate to good yields. Good diastereoselectivities were obtained when using L-valine methyl ester as substrate.

Original language	English
Pages (from-to)	5413-5416
Number of pages	4
Journal	Organic Letters
Volume	9
Issue number	26
DOIs	https://doi.org/10.1021/ol702263b
State	Published - 20 Dec 2007
Externally published	Yes

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abstract = "An efficient system of In/Cul/InCl3 was developed for Barbier-Grignard-type alkylation reactions of simple imines, using a one-pot condensation of various aldehydes, amines (including aliphatic and chiral version), and alkyl iodides in water or aqueous media. The reactions proceeded efficiently at room temperature to give the desired products in moderate to good yields. Good diastereoselectivities were obtained when using L-valine methyl ester as substrate.",

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AU - Loh, Teck Peng

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N2 - An efficient system of In/Cul/InCl3 was developed for Barbier-Grignard-type alkylation reactions of simple imines, using a one-pot condensation of various aldehydes, amines (including aliphatic and chiral version), and alkyl iodides in water or aqueous media. The reactions proceeded efficiently at room temperature to give the desired products in moderate to good yields. Good diastereoselectivities were obtained when using L-valine methyl ester as substrate.

AB - An efficient system of In/Cul/InCl3 was developed for Barbier-Grignard-type alkylation reactions of simple imines, using a one-pot condensation of various aldehydes, amines (including aliphatic and chiral version), and alkyl iodides in water or aqueous media. The reactions proceeded efficiently at room temperature to give the desired products in moderate to good yields. Good diastereoselectivities were obtained when using L-valine methyl ester as substrate.

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Indium - Copper-mediated barbier - Grignard-type alkylation reaction of imines in aqueous media

Abstract

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