Chiral 1-(1,3-dithian-2-yl) prop-2-en-1-ols: new scaffolds for enantiopure α-hydroxyaldehydes

Masaru Akehi; Mariko Kawamoto; Tadakatsu Mandai

doi:10.1016/j.tet.2015.05.039

Chiral 1-(1,3-dithian-2-yl) prop-2-en-1-ols: new scaffolds for enantiopure α-hydroxyaldehydes

Masaru Akehi, Mariko Kawamoto, Tadakatsu Mandai

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

4 Citations (Scopus)

Abstract

Abstract We have demonstrated that chiral 1-(1,3-dithian-2-yl)prop-2-en-1-ols as new scaffolds, obtained by enzyme-catalyzed kinetic resolution, undergo Suzuki-Miyaura cross-couplings and hydroformylation smoothly. Also, we have found that a 1,3-dithianyl group of the products can be removed without any erosion of the enantiopurity under mild conditions. A new access to a variety of enantiopure α-hydroxyaldehydes with ensured absolute configuration is described.

Original language	English
Article number	26757
Pages (from-to)	6488-6498
Number of pages	11
Journal	Tetrahedron
Volume	71
Issue number	37
DOIs	https://doi.org/10.1016/j.tet.2015.05.039
Publication status	Published - Aug 7 2015
Externally published	Yes

Keywords

1,3-Dipolar cycloaddition
Hydroformylation
Scaffold
Suzuki-Miyaura cross-coupling
α-Hydroxyaldehyde

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "Chiral 1-(1,3-dithian-2-yl) prop-2-en-1-ols: new scaffolds for enantiopure α-hydroxyaldehydes",

abstract = "Abstract We have demonstrated that chiral 1-(1,3-dithian-2-yl)prop-2-en-1-ols as new scaffolds, obtained by enzyme-catalyzed kinetic resolution, undergo Suzuki-Miyaura cross-couplings and hydroformylation smoothly. Also, we have found that a 1,3-dithianyl group of the products can be removed without any erosion of the enantiopurity under mild conditions. A new access to a variety of enantiopure α-hydroxyaldehydes with ensured absolute configuration is described.",

keywords = "1,3-Dipolar cycloaddition, Hydroformylation, Scaffold, Suzuki-Miyaura cross-coupling, α-Hydroxyaldehyde",

author = "Masaru Akehi and Mariko Kawamoto and Tadakatsu Mandai",

year = "2015",

month = aug,

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doi = "10.1016/j.tet.2015.05.039",

language = "English",

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T1 - Chiral 1-(1,3-dithian-2-yl) prop-2-en-1-ols

T2 - new scaffolds for enantiopure α-hydroxyaldehydes

AU - Akehi, Masaru

AU - Kawamoto, Mariko

AU - Mandai, Tadakatsu

PY - 2015/8/7

Y1 - 2015/8/7

N2 - Abstract We have demonstrated that chiral 1-(1,3-dithian-2-yl)prop-2-en-1-ols as new scaffolds, obtained by enzyme-catalyzed kinetic resolution, undergo Suzuki-Miyaura cross-couplings and hydroformylation smoothly. Also, we have found that a 1,3-dithianyl group of the products can be removed without any erosion of the enantiopurity under mild conditions. A new access to a variety of enantiopure α-hydroxyaldehydes with ensured absolute configuration is described.

AB - Abstract We have demonstrated that chiral 1-(1,3-dithian-2-yl)prop-2-en-1-ols as new scaffolds, obtained by enzyme-catalyzed kinetic resolution, undergo Suzuki-Miyaura cross-couplings and hydroformylation smoothly. Also, we have found that a 1,3-dithianyl group of the products can be removed without any erosion of the enantiopurity under mild conditions. A new access to a variety of enantiopure α-hydroxyaldehydes with ensured absolute configuration is described.

KW - 1,3-Dipolar cycloaddition

KW - Hydroformylation

KW - Scaffold

KW - Suzuki-Miyaura cross-coupling

KW - α-Hydroxyaldehyde

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DO - 10.1016/j.tet.2015.05.039

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