Palladium-catalyzed diastereoselective synthesis of homoaldol equivalent products

Yoshikazu Horino; Miki Sugata; Tetsu Sugita; Ataru Aimono; Hitoshi Abe

doi:10.1016/j.tetlet.2017.04.064

Palladium-catalyzed diastereoselective synthesis of homoaldol equivalent products

Yoshikazu Horino^*, Miki Sugata, Tetsu Sugita, Ataru Aimono, Hitoshi Abe

^*Corresponding author for this work

Applied Chemistry

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

4 Scopus citations

Abstract

A palladium-catalyzed reaction of easily accessible 3-(pinacolatoboryl)allyl acetates and aldehydes provides facile access to synthetically useful homoaldol equivalent products with high diastereoselectivity. The reaction presumably proceeds via allylation of aldehydes with α-acetoxy allylboronates that produced in situ by reductive elimination from allylic gem-palladium/boryl intermediates.

Original language	English
Pages (from-to)	2131-2134
Number of pages	4
Journal	Tetrahedron Letters
Volume	58
Issue number	22
DOIs	https://doi.org/10.1016/j.tetlet.2017.04.064
State	Published - 2017

Keywords

Allylation
Allylpalladium
Homoaldol equivalent reaction
Palladium catalysis

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2017.04.064

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title = "Palladium-catalyzed diastereoselective synthesis of homoaldol equivalent products",

abstract = "A palladium-catalyzed reaction of easily accessible 3-(pinacolatoboryl)allyl acetates and aldehydes provides facile access to synthetically useful homoaldol equivalent products with high diastereoselectivity. The reaction presumably proceeds via allylation of aldehydes with α-acetoxy allylboronates that produced in situ by reductive elimination from allylic gem-palladium/boryl intermediates.",

keywords = "Allylation, Allylpalladium, Homoaldol equivalent reaction, Palladium catalysis",

author = "Yoshikazu Horino and Miki Sugata and Tetsu Sugita and Ataru Aimono and Hitoshi Abe",

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year = "2017",

doi = "10.1016/j.tetlet.2017.04.064",

language = "英語",

volume = "58",

pages = "2131--2134",

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T1 - Palladium-catalyzed diastereoselective synthesis of homoaldol equivalent products

AU - Horino, Yoshikazu

AU - Sugata, Miki

AU - Sugita, Tetsu

AU - Aimono, Ataru

AU - Abe, Hitoshi

PY - 2017

Y1 - 2017

N2 - A palladium-catalyzed reaction of easily accessible 3-(pinacolatoboryl)allyl acetates and aldehydes provides facile access to synthetically useful homoaldol equivalent products with high diastereoselectivity. The reaction presumably proceeds via allylation of aldehydes with α-acetoxy allylboronates that produced in situ by reductive elimination from allylic gem-palladium/boryl intermediates.

AB - A palladium-catalyzed reaction of easily accessible 3-(pinacolatoboryl)allyl acetates and aldehydes provides facile access to synthetically useful homoaldol equivalent products with high diastereoselectivity. The reaction presumably proceeds via allylation of aldehydes with α-acetoxy allylboronates that produced in situ by reductive elimination from allylic gem-palladium/boryl intermediates.

KW - Allylation

KW - Allylpalladium

KW - Homoaldol equivalent reaction

KW - Palladium catalysis

UR - http://www.scopus.com/inward/record.url?scp=85018196077&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2017.04.064

DO - 10.1016/j.tetlet.2017.04.064

M3 - 学術論文

AN - SCOPUS:85018196077

SN - 0040-4039

VL - 58

SP - 2131

EP - 2134

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 22

ER -

Palladium-catalyzed diastereoselective synthesis of homoaldol equivalent products

Abstract

Keywords

ASJC Scopus subject areas

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