Facile synthesis of (Z)-anti-homoallylic alcohols from 3-(pinacolatoboryl)allyl alcohols, aldehydes, and triorganoboranes via a palladium-catalyzed three-component reaction

Yoshikazu Horino; Ataru Aimono; Naoki Minoshima; Hitoshi Abe

doi:10.1016/j.tetlet.2016.06.121

Facile synthesis of (Z)-anti-homoallylic alcohols from 3-(pinacolatoboryl)allyl alcohols, aldehydes, and triorganoboranes via a palladium-catalyzed three-component reaction

Yoshikazu Horino^*, Ataru Aimono, Naoki Minoshima, Hitoshi Abe

^*この論文の責任著者

工学科　応用化学コース

研究成果: ジャーナルへの寄稿 › 学術論文 › 査読

2 被引用数 (Scopus)

抄録

A palladium-catalyzed three-component reaction of 3-(pinacolatoboryl)allyl alcohols, aldehydes, and triorganoboranes was developed. The present protocol provides facile access to synthetically useful (Z)-anti-homoallylic alcohols with high diastereoselectivity and high levels of alkene stereocontrol. Furthermore, single-flask reaction sequences to synthesize (Z)-anti-homoallylic alcohols starting from propargyl alcohols by using palladium-catalyzed three-component reaction are successfully achieved.

本文言語	英語
ページ（範囲）	3561-3564
ページ数	4
ジャーナル	Tetrahedron Letters
巻	57
号	31
DOI	https://doi.org/10.1016/j.tetlet.2016.06.121
出版ステータス	出版済み - 2016

ASJC Scopus 主題領域

生化学
創薬
有機化学

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10.1016/j.tetlet.2016.06.121

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引用スタイル

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title = "Facile synthesis of (Z)-anti-homoallylic alcohols from 3-(pinacolatoboryl)allyl alcohols, aldehydes, and triorganoboranes via a palladium-catalyzed three-component reaction",

abstract = "A palladium-catalyzed three-component reaction of 3-(pinacolatoboryl)allyl alcohols, aldehydes, and triorganoboranes was developed. The present protocol provides facile access to synthetically useful (Z)-anti-homoallylic alcohols with high diastereoselectivity and high levels of alkene stereocontrol. Furthermore, single-flask reaction sequences to synthesize (Z)-anti-homoallylic alcohols starting from propargyl alcohols by using palladium-catalyzed three-component reaction are successfully achieved.",

keywords = "Allylation, Homoallylic alcohols, Palladium catalysis, Three-component reaction",

author = "Yoshikazu Horino and Ataru Aimono and Naoki Minoshima and Hitoshi Abe",

note = "Publisher Copyright: {\textcopyright} 2016 Elsevier Ltd",

year = "2016",

doi = "10.1016/j.tetlet.2016.06.121",

language = "英語",

volume = "57",

pages = "3561--3564",

journal = "Tetrahedron Letters",

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TY - JOUR

T1 - Facile synthesis of (Z)-anti-homoallylic alcohols from 3-(pinacolatoboryl)allyl alcohols, aldehydes, and triorganoboranes via a palladium-catalyzed three-component reaction

AU - Horino, Yoshikazu

AU - Aimono, Ataru

AU - Minoshima, Naoki

AU - Abe, Hitoshi

PY - 2016

Y1 - 2016

N2 - A palladium-catalyzed three-component reaction of 3-(pinacolatoboryl)allyl alcohols, aldehydes, and triorganoboranes was developed. The present protocol provides facile access to synthetically useful (Z)-anti-homoallylic alcohols with high diastereoselectivity and high levels of alkene stereocontrol. Furthermore, single-flask reaction sequences to synthesize (Z)-anti-homoallylic alcohols starting from propargyl alcohols by using palladium-catalyzed three-component reaction are successfully achieved.

AB - A palladium-catalyzed three-component reaction of 3-(pinacolatoboryl)allyl alcohols, aldehydes, and triorganoboranes was developed. The present protocol provides facile access to synthetically useful (Z)-anti-homoallylic alcohols with high diastereoselectivity and high levels of alkene stereocontrol. Furthermore, single-flask reaction sequences to synthesize (Z)-anti-homoallylic alcohols starting from propargyl alcohols by using palladium-catalyzed three-component reaction are successfully achieved.

KW - Allylation

KW - Homoallylic alcohols

KW - Palladium catalysis

KW - Three-component reaction

UR - http://www.scopus.com/inward/record.url?scp=84979049890&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2016.06.121

DO - 10.1016/j.tetlet.2016.06.121

M3 - 学術論文

AN - SCOPUS:84979049890

SN - 0040-4039

VL - 57

SP - 3561

EP - 3564

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 31

ER -