An efficient partial reduction of α,β-unsaturated esters using DIBAL-H in flow

Masahito Yoshida; Hiroyuki Otaka; Takayuki Doi

doi:10.1002/ejoc.201402675

An efficient partial reduction of α,β-unsaturated esters using DIBAL-H in flow

Masahito Yoshida, Hiroyuki Otaka, Takayuki Doi

PHA - Molecular Pharmaceutical Science

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

13 Citations (Scopus)

Abstract

The partial reduction of α,β-unsaturated esters and benzoate derivatives to form the corresponding aldehydes was achieved using a flow reactor system within 1 s at a high flow rate (18 mL min^-1) under cryogenic conditions (-97°C). Commercially available diisobutylaluminium hydride (DIBAL-H) was used as the reductant. The desired enals and benzaldehyde derivatives, except for 4-methoxycinnamate and 4-methoxybenzoate, were formed selectively and redox economically in moderate to high yields.

Original language	English
Pages (from-to)	6010-6016
Number of pages	7
Journal	European Journal of Organic Chemistry
Volume	2014
Issue number	27
DOIs	https://doi.org/10.1002/ejoc.201402675
Publication status	Published - 2014 Sept

Keywords

Aldehydes
Chemoselectivity
Esters
Flow synthesis
Reduction

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry

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10.1002/ejoc.201402675

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abstract = "The partial reduction of α,β-unsaturated esters and benzoate derivatives to form the corresponding aldehydes was achieved using a flow reactor system within 1 s at a high flow rate (18 mL min-1) under cryogenic conditions (-97°C). Commercially available diisobutylaluminium hydride (DIBAL-H) was used as the reductant. The desired enals and benzaldehyde derivatives, except for 4-methoxycinnamate and 4-methoxybenzoate, were formed selectively and redox economically in moderate to high yields.",

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AU - Yoshida, Masahito

AU - Otaka, Hiroyuki

AU - Doi, Takayuki

PY - 2014/9

Y1 - 2014/9

N2 - The partial reduction of α,β-unsaturated esters and benzoate derivatives to form the corresponding aldehydes was achieved using a flow reactor system within 1 s at a high flow rate (18 mL min-1) under cryogenic conditions (-97°C). Commercially available diisobutylaluminium hydride (DIBAL-H) was used as the reductant. The desired enals and benzaldehyde derivatives, except for 4-methoxycinnamate and 4-methoxybenzoate, were formed selectively and redox economically in moderate to high yields.

AB - The partial reduction of α,β-unsaturated esters and benzoate derivatives to form the corresponding aldehydes was achieved using a flow reactor system within 1 s at a high flow rate (18 mL min-1) under cryogenic conditions (-97°C). Commercially available diisobutylaluminium hydride (DIBAL-H) was used as the reductant. The desired enals and benzaldehyde derivatives, except for 4-methoxycinnamate and 4-methoxybenzoate, were formed selectively and redox economically in moderate to high yields.

KW - Aldehydes

KW - Chemoselectivity

KW - Esters

KW - Flow synthesis

KW - Reduction

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M3 - Article

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JO - Justus Liebigs Annalen der Chemie

JF - Justus Liebigs Annalen der Chemie

IS - 27

ER -

An efficient partial reduction of α,β-unsaturated esters using DIBAL-H in flow

Abstract

Keywords

ASJC Scopus subject areas

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