Formation of α-hydroxyketones via irregular Wittig reaction

Hideki Okada; Tomonori Mori; Yoko Saikawa; Masaya Nakata

doi:10.1016/j.tetlet.2008.12.102

Formation of α-hydroxyketones via irregular Wittig reaction

Hideki Okada, Tomonori Mori, Yoko Saikawa, Masaya Nakata

Department of Applied Chemistry

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

13 Citations (Scopus)

Abstract

Αddition reactions of (1-methoxyalkyl)triphenylphosphonium ylides, derived from the corresponding Wittig salts and n-BuLi, to aldehydes were investigated. It was revealed that the betaine LiX complexes, the primary adducts, were converted to α-hydroxyketones, prior to the formation of oxaphosphetanes, by addition of aqueous NH₄Cl at low temperature.

Original language	English
Pages (from-to)	1276-1278
Number of pages	3
Journal	Tetrahedron Letters
Volume	50
Issue number	12
DOIs	https://doi.org/10.1016/j.tetlet.2008.12.102
Publication status	Published - 2009 Mar 25

Keywords

(1-Methoxyalkyl)triphenylphosphonium ylide
Acyl anion equivalent
Wittig reaction
α-Hydroxyketone

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2008.12.102

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abstract = "Αddition reactions of (1-methoxyalkyl)triphenylphosphonium ylides, derived from the corresponding Wittig salts and n-BuLi, to aldehydes were investigated. It was revealed that the betaine LiX complexes, the primary adducts, were converted to α-hydroxyketones, prior to the formation of oxaphosphetanes, by addition of aqueous NH4Cl at low temperature.",

keywords = "(1-Methoxyalkyl)triphenylphosphonium ylide, Acyl anion equivalent, Wittig reaction, α-Hydroxyketone",

author = "Hideki Okada and Tomonori Mori and Yoko Saikawa and Masaya Nakata",

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T1 - Formation of α-hydroxyketones via irregular Wittig reaction

AU - Okada, Hideki

AU - Mori, Tomonori

AU - Saikawa, Yoko

AU - Nakata, Masaya

PY - 2009/3/25

Y1 - 2009/3/25

N2 - Αddition reactions of (1-methoxyalkyl)triphenylphosphonium ylides, derived from the corresponding Wittig salts and n-BuLi, to aldehydes were investigated. It was revealed that the betaine LiX complexes, the primary adducts, were converted to α-hydroxyketones, prior to the formation of oxaphosphetanes, by addition of aqueous NH4Cl at low temperature.

AB - Αddition reactions of (1-methoxyalkyl)triphenylphosphonium ylides, derived from the corresponding Wittig salts and n-BuLi, to aldehydes were investigated. It was revealed that the betaine LiX complexes, the primary adducts, were converted to α-hydroxyketones, prior to the formation of oxaphosphetanes, by addition of aqueous NH4Cl at low temperature.

KW - (1-Methoxyalkyl)triphenylphosphonium ylide

KW - Acyl anion equivalent

KW - Wittig reaction

KW - α-Hydroxyketone

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DO - 10.1016/j.tetlet.2008.12.102

M3 - Article

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VL - 50

SP - 1276

EP - 1278

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 12

ER -

Formation of α-hydroxyketones via irregular Wittig reaction

Abstract

Keywords

ASJC Scopus subject areas

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