Indium(III) chloride-catalyzed Mukaiyama-Michael addition: Synthesis of 2,6-anti-tetrahydropyrans

Sin Siu Chua; Anita Alni; Li Ting Jocelyn Chan; Motoki Yamane; Teck Peng Loh

doi:10.1016/j.tet.2011.04.101

Indium(III) chloride-catalyzed Mukaiyama-Michael addition: Synthesis of 2,6-anti-tetrahydropyrans

Sin Siu Chua, Anita Alni, Li Ting Jocelyn Chan, Motoki Yamane^*, Teck Peng Loh

^*Corresponding author for this work

Nanyang Technological University

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

16 Citations (Scopus)

Abstract

In the presence of a catalytic amount of indium(III) chloride (InCl ₃), silyl enol ethers react with dihydropyranones at ambient temperature via Mukaiyama-Michael addition to afford the corresponding 2,6-anti-tetrahydropyran adducts in moderate to good yields. This simple and mild method proceeds under neat conditions and involves simple aqueous work-up. Indium(III) chloride can be recovered and reused without significant decrease in reactivity.

Original language	English
Pages (from-to)	5079-5082
Number of pages	4
Journal	Tetrahedron
Volume	67
Issue number	27-28
DOIs	https://doi.org/10.1016/j.tet.2011.04.101
Publication status	Published - Jul 8 2011
Externally published	Yes

ASJC Scopus Subject Areas

Biochemistry
Drug Discovery
Organic Chemistry

Keywords

2,6-Anti-tetrahydropyran
Indium(III) chloride
Mukaiyama-Michael addition
Neat conditions

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10.1016/j.tet.2011.04.101

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title = "Indium(III) chloride-catalyzed Mukaiyama-Michael addition: Synthesis of 2,6-anti-tetrahydropyrans",

abstract = "In the presence of a catalytic amount of indium(III) chloride (InCl 3), silyl enol ethers react with dihydropyranones at ambient temperature via Mukaiyama-Michael addition to afford the corresponding 2,6-anti-tetrahydropyran adducts in moderate to good yields. This simple and mild method proceeds under neat conditions and involves simple aqueous work-up. Indium(III) chloride can be recovered and reused without significant decrease in reactivity.",

keywords = "2,6-Anti-tetrahydropyran, Indium(III) chloride, Mukaiyama-Michael addition, Neat conditions",

author = "Chua, \{Sin Siu\} and Anita Alni and \{Jocelyn Chan\}, \{Li Ting\} and Motoki Yamane and Loh, \{Teck Peng\}",

year = "2011",

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doi = "10.1016/j.tet.2011.04.101",

language = "English",

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journal = "Tetrahedron",

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T1 - Indium(III) chloride-catalyzed Mukaiyama-Michael addition

T2 - Synthesis of 2,6-anti-tetrahydropyrans

AU - Chua, Sin Siu

AU - Alni, Anita

AU - Jocelyn Chan, Li Ting

AU - Yamane, Motoki

AU - Loh, Teck Peng

PY - 2011/7/8

Y1 - 2011/7/8

N2 - In the presence of a catalytic amount of indium(III) chloride (InCl 3), silyl enol ethers react with dihydropyranones at ambient temperature via Mukaiyama-Michael addition to afford the corresponding 2,6-anti-tetrahydropyran adducts in moderate to good yields. This simple and mild method proceeds under neat conditions and involves simple aqueous work-up. Indium(III) chloride can be recovered and reused without significant decrease in reactivity.

AB - In the presence of a catalytic amount of indium(III) chloride (InCl 3), silyl enol ethers react with dihydropyranones at ambient temperature via Mukaiyama-Michael addition to afford the corresponding 2,6-anti-tetrahydropyran adducts in moderate to good yields. This simple and mild method proceeds under neat conditions and involves simple aqueous work-up. Indium(III) chloride can be recovered and reused without significant decrease in reactivity.

KW - 2,6-Anti-tetrahydropyran

KW - Indium(III) chloride

KW - Mukaiyama-Michael addition

KW - Neat conditions

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DO - 10.1016/j.tet.2011.04.101

M3 - Article

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VL - 67

SP - 5079

EP - 5082

JO - Tetrahedron

JF - Tetrahedron

IS - 27-28

ER -

Indium(III) chloride-catalyzed Mukaiyama-Michael addition: Synthesis of 2,6-anti-tetrahydropyrans

Abstract

ASJC Scopus Subject Areas

Keywords

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