A remote substituent as a control element in indium-mediated allylation reactions in aqueous media: Highly diastereoselective synthesis of 1,3-amino alcohols

Teck Peng Loh; Jing Mei Huang; Kai Chen Xu; Swee Hock Goh; Jagadese J. Vittal

doi:10.1016/S0040-4039(00)01040-6

A remote substituent as a control element in indium-mediated allylation reactions in aqueous media: Highly diastereoselective synthesis of 1,3-amino alcohols

Teck Peng Loh, Jing Mei Huang, Kai Chen Xu, Swee Hock Goh, Jagadese J. Vittal

National University of Singapore

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

30 Citations (Scopus)

Abstract

A new method for the stereoselective synthesis of 1,3-amino alcohols based on the indium-mediated allylation of keto ester (R, S)-2 in aqueous media, resulting from shielding of one face by a remote substituent, was developed to be a useful method for acyclic stereocontrol in the absence of any obvious steric interaction.

Original language	English
Pages (from-to)	6511-6515
Number of pages	5
Journal	Tetrahedron Letters
Volume	41
Issue number	33
DOIs	https://doi.org/10.1016/S0040-4039(00)01040-6
Publication status	Published - Aug 12 2000
Externally published	Yes

ASJC Scopus Subject Areas

Biochemistry
Drug Discovery
Organic Chemistry

Keywords

1,3-amino alcohols
Allylation
High diastereoselectivity
Indium
Remote substituent

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10.1016/S0040-4039(00)01040-6

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abstract = "A new method for the stereoselective synthesis of 1,3-amino alcohols based on the indium-mediated allylation of keto ester (R, S)-2 in aqueous media, resulting from shielding of one face by a remote substituent, was developed to be a useful method for acyclic stereocontrol in the absence of any obvious steric interaction.",

keywords = "1,3-amino alcohols, Allylation, High diastereoselectivity, Indium, Remote substituent",

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T2 - Highly diastereoselective synthesis of 1,3-amino alcohols

AU - Loh, Teck Peng

AU - Huang, Jing Mei

AU - Xu, Kai Chen

AU - Goh, Swee Hock

AU - Vittal, Jagadese J.

PY - 2000/8/12

Y1 - 2000/8/12

N2 - A new method for the stereoselective synthesis of 1,3-amino alcohols based on the indium-mediated allylation of keto ester (R, S)-2 in aqueous media, resulting from shielding of one face by a remote substituent, was developed to be a useful method for acyclic stereocontrol in the absence of any obvious steric interaction.

AB - A new method for the stereoselective synthesis of 1,3-amino alcohols based on the indium-mediated allylation of keto ester (R, S)-2 in aqueous media, resulting from shielding of one face by a remote substituent, was developed to be a useful method for acyclic stereocontrol in the absence of any obvious steric interaction.

KW - 1,3-amino alcohols

KW - Allylation

KW - High diastereoselectivity

KW - Indium

KW - Remote substituent

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SN - 0040-4039

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 33

ER -

A remote substituent as a control element in indium-mediated allylation reactions in aqueous media: Highly diastereoselective synthesis of 1,3-amino alcohols

Abstract

ASJC Scopus Subject Areas

Keywords

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