Rhodium-catalyzed reaction of 1-alkenylboronates with aldehydes leading to allylation products

Hiroshi Shimizu; Tomohiro Igarashi; Tomoya Miura; Masahiro Murakami

doi:10.1002/anie.201105148

Rhodium-catalyzed reaction of 1-alkenylboronates with aldehydes leading to allylation products

Hiroshi Shimizu, Tomohiro Igarashi, Tomoya Miura, Masahiro Murakami

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

39 Citations (Scopus)

Abstract

Synthetic equivalents: 1-Alkenylboronates perform the role of an allylating reagent. Their reaction with aldehydes in the presence of a cationic rhodium(I)/dppm catalyst results in a highly diastereoselective production of anti-configured homoallylic alcohols (see scheme; Bpin=4,4,5,5-tetramethyl-1,3, 2-dioxaborolanyl).

Original language	English
Pages (from-to)	11465-11469
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	50
Issue number	48
DOIs	https://doi.org/10.1002/anie.201105148
Publication status	Published - Nov 25 2011
Externally published	Yes

Keywords

aldehydes
allylation
diastereoselectivity
isomerization
rhodium

ASJC Scopus subject areas

Catalysis
Chemistry(all)

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10.1002/anie.201105148

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abstract = "Synthetic equivalents: 1-Alkenylboronates perform the role of an allylating reagent. Their reaction with aldehydes in the presence of a cationic rhodium(I)/dppm catalyst results in a highly diastereoselective production of anti-configured homoallylic alcohols (see scheme; Bpin=4,4,5,5-tetramethyl-1,3, 2-dioxaborolanyl).",

keywords = "aldehydes, allylation, diastereoselectivity, isomerization, rhodium",

author = "Hiroshi Shimizu and Tomohiro Igarashi and Tomoya Miura and Masahiro Murakami",

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doi = "10.1002/anie.201105148",

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journal = "Angewandte Chemie - International Edition",

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T1 - Rhodium-catalyzed reaction of 1-alkenylboronates with aldehydes leading to allylation products

AU - Shimizu, Hiroshi

AU - Igarashi, Tomohiro

AU - Miura, Tomoya

AU - Murakami, Masahiro

PY - 2011/11/25

Y1 - 2011/11/25

N2 - Synthetic equivalents: 1-Alkenylboronates perform the role of an allylating reagent. Their reaction with aldehydes in the presence of a cationic rhodium(I)/dppm catalyst results in a highly diastereoselective production of anti-configured homoallylic alcohols (see scheme; Bpin=4,4,5,5-tetramethyl-1,3, 2-dioxaborolanyl).

AB - Synthetic equivalents: 1-Alkenylboronates perform the role of an allylating reagent. Their reaction with aldehydes in the presence of a cationic rhodium(I)/dppm catalyst results in a highly diastereoselective production of anti-configured homoallylic alcohols (see scheme; Bpin=4,4,5,5-tetramethyl-1,3, 2-dioxaborolanyl).

KW - aldehydes

KW - allylation

KW - diastereoselectivity

KW - isomerization

KW - rhodium

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DO - 10.1002/anie.201105148

M3 - Article

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JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 48

ER -

Rhodium-catalyzed reaction of 1-alkenylboronates with aldehydes leading to allylation products

Abstract

Keywords

ASJC Scopus subject areas

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