Aluminum iodide promoted highly Z-stereoselective synthesis of β-iodo Morita-Baylis-Hillman esters with ketones as aldol acceptors

Sung Il Lee; Geum Sook Hwang; Do Hyun Ryu

doi:10.1055/s-2006-958421

Aluminum iodide promoted highly Z-stereoselective synthesis of β-iodo Morita-Baylis-Hillman esters with ketones as aldol acceptors

Sung Il Lee, Geum Sook Hwang, Do Hyun Ryu

Department of Chemistry

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

17 Scopus citations

Abstract

Aluminum iodide has been found to promote the efficient and highly stereoselective synthesis of (Z)-β-iodo-α-(hydroxyalkyl)acrylates via one-pot three-component coupling reactions. This new system has made it possible to utilize various ketones as the electrophiles, in order to react with an aluminum allenoate intermediate for the synthesis of β-iodo Morita-Baylis-Hillman adducts with high yield and excellent Z-stereoselectivity (>99%).

Original language	English
Pages (from-to)	59-62
Number of pages	4
Journal	Synlett
Issue number	1
DOIs	https://doi.org/10.1055/s-2006-958421
State	Published - 4 Jan 2007

Keywords

Aldol reactions
Aluminum iodide
Ketones
Morita-Baylis-Hillman adduct
Stereoselectivity

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10.1055/s-2006-958421

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title = "Aluminum iodide promoted highly Z-stereoselective synthesis of β-iodo Morita-Baylis-Hillman esters with ketones as aldol acceptors",

abstract = "Aluminum iodide has been found to promote the efficient and highly stereoselective synthesis of (Z)-β-iodo-α-(hydroxyalkyl)acrylates via one-pot three-component coupling reactions. This new system has made it possible to utilize various ketones as the electrophiles, in order to react with an aluminum allenoate intermediate for the synthesis of β-iodo Morita-Baylis-Hillman adducts with high yield and excellent Z-stereoselectivity (>99\%).",

keywords = "Aldol reactions, Aluminum iodide, Ketones, Morita-Baylis-Hillman adduct, Stereoselectivity",

author = "Lee, \{Sung Il\} and Hwang, \{Geum Sook\} and Ryu, \{Do Hyun\}",

year = "2007",

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doi = "10.1055/s-2006-958421",

language = "English",

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AU - Lee, Sung Il

AU - Hwang, Geum Sook

AU - Ryu, Do Hyun

PY - 2007/1/4

Y1 - 2007/1/4

N2 - Aluminum iodide has been found to promote the efficient and highly stereoselective synthesis of (Z)-β-iodo-α-(hydroxyalkyl)acrylates via one-pot three-component coupling reactions. This new system has made it possible to utilize various ketones as the electrophiles, in order to react with an aluminum allenoate intermediate for the synthesis of β-iodo Morita-Baylis-Hillman adducts with high yield and excellent Z-stereoselectivity (>99%).

AB - Aluminum iodide has been found to promote the efficient and highly stereoselective synthesis of (Z)-β-iodo-α-(hydroxyalkyl)acrylates via one-pot three-component coupling reactions. This new system has made it possible to utilize various ketones as the electrophiles, in order to react with an aluminum allenoate intermediate for the synthesis of β-iodo Morita-Baylis-Hillman adducts with high yield and excellent Z-stereoselectivity (>99%).

KW - Aldol reactions

KW - Aluminum iodide

KW - Ketones

KW - Morita-Baylis-Hillman adduct

KW - Stereoselectivity

UR - https://www.scopus.com/pages/publications/33846439385

U2 - 10.1055/s-2006-958421

DO - 10.1055/s-2006-958421

M3 - Article

AN - SCOPUS:33846439385

SN - 0936-5214

SP - 59

EP - 62

JO - Synlett

JF - Synlett

IS - 1

ER -

Aluminum iodide promoted highly Z-stereoselective synthesis of β-iodo Morita-Baylis-Hillman esters with ketones as aldol acceptors

Abstract

Keywords

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