Asymmetric Synthesis of Dihydropyranones with Three Contiguous Stereocenters by an NHC-Catalyzed Kinetic Resolution

Axelsson, Anton, 1991 (author): Chalmers tekniska högskola,Chalmers University of Technology

Westerlund, M. (author): Chalmers tekniska högskola,Chalmers University of Technology

Zacharias, Savannah C. (author): Gothenburg University,Göteborgs universitet,Institutionen för kemi och molekylärbiologi,Department of Chemistry and Molecular Biology,University of Gothenburg

Runemark, August, 1993 (author): Chalmers tekniska högskola,Chalmers University of Technology

Sundén, Henrik, 1978 (author): Gothenburg University,Göteborgs universitet,Institutionen för kemi och molekylärbiologi,Department of Chemistry and Molecular Biology,University of Gothenburg,Chalmers tekniska högskola,Chalmers University of Technology

(creator_code:org_t)

2021-07-06
2021
English.
In: European Journal of Organic Chemistry. - : Wiley. - 1434-193X .- 1099-0690. ; 2021:25, s. 3657-3661

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Abstract Subject headings

An oxidative NHC-catalyzed kinetic resolution (KR) of racemic mixtures is presented. The developed reaction furnishes tricyclic dihydropyranones with three contiguous stereocenters in excellent dia- and enantioselectivity, with good-to-moderate yields. Mechanistic studies indicate that the rate-determining step of the reaction is the formation of the Breslow intermediate, while the selectivity determining step occurs later in the mechanism. The presented methodology enables rapid synthesis of complex structures in a single step.

NATURVETENSKAP -- Kemi (hsv//swe)
NATURAL SCIENCES -- Chemical Sciences (hsv//eng)
NATURVETENSKAP -- Kemi -- Oorganisk kemi (hsv//swe)
NATURAL SCIENCES -- Chemical Sciences -- Inorganic Chemistry (hsv//eng)
TEKNIK OCH TEKNOLOGIER -- Industriell bioteknik -- Biokatalys och enzymteknik (hsv//swe)
ENGINEERING AND TECHNOLOGY -- Industrial Biotechnology -- Biocatalysis and Enzyme Technology (hsv//eng)
NATURVETENSKAP -- Kemi -- Organisk kemi (hsv//swe)
NATURAL SCIENCES -- Chemical Sciences -- Organic Chemistry (hsv//eng)

By the author/editor: Axelsson, Anton, ...; Westerlund, M.; Zacharias, Savan ...; Runemark, August ...; Haukka, M.; Sundén, Henrik, ...

About the subject

NATURAL SCIENCES: NATURAL SCIENCES; and Chemical Science ...; and Inorganic Chemis ...

ENGINEERING AND TECHNOLOGY: ENGINEERING AND ...; and Industrial Biote ...; and Biocatalysis and ...

NATURAL SCIENCES: NATURAL SCIENCES; and Chemical Science ...; and Organic Chemistr ...

By the university: University of Gothenburg; Chalmers University of Technology

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