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

応用化学科

研究成果: Article › 査読

13 被引用数 (Scopus)

抄録

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.

本文言語	English
ページ（範囲）	1276-1278
ページ数	3
ジャーナル	Tetrahedron Letters
巻	50
号	12
DOI	https://doi.org/10.1016/j.tetlet.2008.12.102
出版ステータス	Published - 2009 3 25

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2008.12.102

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引用スタイル

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

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

year = "2009",

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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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