Palladium-catalyzed cyclopropanation of strained alkenes with 3-pinacolatoboryl-1-arylallyl carboxylates

Yoshikazu Horino; Yu Takahashi; Ryota Kobayashi; Hitoshi Abe

doi:10.1002/ejoc.201403284

Palladium-catalyzed cyclopropanation of strained alkenes with 3-pinacolatoboryl-1-arylallyl carboxylates

Yoshikazu Horino^*, Yu Takahashi, Ryota Kobayashi, Hitoshi Abe

^*Corresponding author for this work

Applied Chemistry

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

6 Scopus citations

Abstract

The palladium-catalyzed cyclopropanation of strained alkenes with 3-pinacolatoboryl-1-arylallyl carboxylates was explored. The reactions proceeded smoothly under mild conditions, and the cyclopropanation products were obtained in good to high yields with high diastereoselectivities if CsF, 18-crown-6, and molecular sieves were used as additives. The reaction was hypothesized to proceed through the formation of a putative palladacyclobutene intermediate that needed to be considered to explain the observed stereochemistry.

Original language	English
Pages (from-to)	7818-7822
Number of pages	5
Journal	European Journal of Organic Chemistry
Volume	2014
Issue number	35
DOIs	https://doi.org/10.1002/ejoc.201403284
State	Published - 2014/11/10

Keywords

Carbenoids
Cyclopropanation
Isomerization
Palladium

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry

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10.1002/ejoc.201403284

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title = "Palladium-catalyzed cyclopropanation of strained alkenes with 3-pinacolatoboryl-1-arylallyl carboxylates",

abstract = "The palladium-catalyzed cyclopropanation of strained alkenes with 3-pinacolatoboryl-1-arylallyl carboxylates was explored. The reactions proceeded smoothly under mild conditions, and the cyclopropanation products were obtained in good to high yields with high diastereoselectivities if CsF, 18-crown-6, and molecular sieves were used as additives. The reaction was hypothesized to proceed through the formation of a putative palladacyclobutene intermediate that needed to be considered to explain the observed stereochemistry.",

keywords = "Carbenoids, Cyclopropanation, Isomerization, Palladium",

author = "Yoshikazu Horino and Yu Takahashi and Ryota Kobayashi and Hitoshi Abe",

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T1 - Palladium-catalyzed cyclopropanation of strained alkenes with 3-pinacolatoboryl-1-arylallyl carboxylates

AU - Horino, Yoshikazu

AU - Takahashi, Yu

AU - Kobayashi, Ryota

AU - Abe, Hitoshi

PY - 2014/11/10

Y1 - 2014/11/10

N2 - The palladium-catalyzed cyclopropanation of strained alkenes with 3-pinacolatoboryl-1-arylallyl carboxylates was explored. The reactions proceeded smoothly under mild conditions, and the cyclopropanation products were obtained in good to high yields with high diastereoselectivities if CsF, 18-crown-6, and molecular sieves were used as additives. The reaction was hypothesized to proceed through the formation of a putative palladacyclobutene intermediate that needed to be considered to explain the observed stereochemistry.

AB - The palladium-catalyzed cyclopropanation of strained alkenes with 3-pinacolatoboryl-1-arylallyl carboxylates was explored. The reactions proceeded smoothly under mild conditions, and the cyclopropanation products were obtained in good to high yields with high diastereoselectivities if CsF, 18-crown-6, and molecular sieves were used as additives. The reaction was hypothesized to proceed through the formation of a putative palladacyclobutene intermediate that needed to be considered to explain the observed stereochemistry.

KW - Carbenoids

KW - Cyclopropanation

KW - Isomerization

KW - Palladium

UR - http://www.scopus.com/inward/record.url?scp=84918781831&partnerID=8YFLogxK

U2 - 10.1002/ejoc.201403284

DO - 10.1002/ejoc.201403284

M3 - 学術論文

AN - SCOPUS:84918781831

SN - 1434-193X

VL - 2014

SP - 7818

EP - 7822

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 35

ER -

Palladium-catalyzed cyclopropanation of strained alkenes with 3-pinacolatoboryl-1-arylallyl carboxylates

Abstract

Keywords

ASJC Scopus subject areas

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