ChemInform Abstract: Kinetic Resolution of Racemic Secondary Alcohols by Ru(II)-Catalyzed Hydrogen Transfer.

No matter through asymmetric reduction of ketones or kinetic resolution of secondary alcohols, enantioselective synthesis of the corresponding secondary alcohols is challenging when the two groups attached to the prochiral or chiral centers are spatially or electronically similar. For examples, dialkyl (sp3 vs. sp3), diaryl (sp2 vs. sp2), and aryl-alkenyl (sp2 vs. sp2) alcohols are difficult to produce with high enantioselectivities. By exploiting our recently developed Ru-catalysts of minimal stereogenicity, we reported herein a highly efficient kinetic resolution of aryl-alkenyl alcohols through hydrogen transfer. This method enabled such versatile chiral building blocks for organic synthesis as allylic alcohols, to be readily accessed with excellent enantiomeric excesses at practically useful conversions.

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Kinetic resolution of sterically hindered secondary alcohols catalyzed by aminophosphinite organocatalyst

Tetrahedron ◽

10.1016/j.tet.2017.11.062 ◽

2018 ◽

Vol 74 (2) ◽

pp. 296-302 ◽

Cited By ~ 1

Author(s):

Nanami Hara ◽

Shu Fujisawa ◽

Mizuki Fujita ◽

Mikako Miyazawa ◽

Kazuma Ochiai ◽

...

Keyword(s):

Kinetic Resolution ◽

Secondary Alcohols ◽

Sterically Hindered

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Kinetic Resolution of Chiral Secondary Alcohols by Dehydrogenative Coupling with Recyclable Silicon-Stereogenic Silanes

Angewandte Chemie International Edition ◽

10.1002/anie.200502631 ◽

2005 ◽

Vol 44 (46) ◽

pp. 7620-7624 ◽

Cited By ~ 121

Author(s):

Sebastian Rendler ◽

Gertrud Auer ◽

Martin Oestreich

Keyword(s):

Kinetic Resolution ◽

Secondary Alcohols ◽

Dehydrogenative Coupling

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ChemInform Abstract: Kinetic Resolution of Racemic Secondary Alcohols via Oxidation with Yarrowia lipolytica Strains.

ChemInform ◽

10.1002/chin.200040033 ◽

2000 ◽

Vol 31 (40) ◽

pp. no-no

Author(s):

Giancarlo Fantin ◽

Marco Fogagnolo ◽

Alessandro Medici ◽

Paola Pedrini ◽

Silvia Fontana

Keyword(s):

Yarrowia Lipolytica ◽

Kinetic Resolution ◽

Secondary Alcohols

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Scalable Green Approach Toward Fragrant Acetates

Molecules ◽

10.3390/molecules25143217 ◽

2020 ◽

Vol 25 (14) ◽

pp. 3217

Author(s):

Eva Puchl’ová ◽

Peter Szolcsányi

Keyword(s):

Kinetic Resolution ◽

High Reactivity ◽

Secondary Alcohols ◽

Enzymatic System ◽

Single Product ◽

Discrimination Power ◽

Green Approach ◽

Naturally Occurring ◽

Glycerol Triacetate ◽

Practical Synthesis

The advantageous properties of ethylene glycol diacetate (EGDA) qualify it as a useful substitute for glycerol triacetate (GTA) for various green applications. We scrutinised the lipase-mediated acetylation of structurally diverse alcohols in neat EGDA furnishing the range of naturally occurring fragrant acetates. We found that such enzymatic system exhibits high reactivity and selectivity towards activated (homo) allylic and non-activated primary/secondary alcohols. This feature was utilised in the scalable multigram synthesis of fragrant (Z)-hex-3-en-1-yl acetate in 70% yield. In addition, the Lipozyme 435/EGDA system was also found to be applicable for the chemo-selective acetylation of (hydroxyalkyl) phenols as well as for the kinetic resolution of chiral secondary alcohols. Lastly, its discrimination power was demonstrated in competitive experiments of equimolar mixtures of two isomeric alcohols. This enabled the practical synthesis of 1-pentyl acetate isolated as a single product in 68% yield from the equimolar mixture of 1-pentanol and 3-pentanol.

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