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

3 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

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Keywords

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

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Cite this

Akehi, M., Kawamoto, M., & Mandai, T. (2015). Chiral 1-(1,3-dithian-2-yl) prop-2-en-1-ols: new scaffolds for enantiopure α-hydroxyaldehydes. Tetrahedron, 71(37), 6488-6498. [26757]. https://doi.org/10.1016/j.tet.2015.05.039

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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.",

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AU - Mandai, Tadakatsu

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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.

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KW - Suzuki-Miyaura cross-coupling

KW - α-Hydroxyaldehyde

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10.1016/j.tet.2015.05.039