111138-02-4Relevant articles and documents
Biotransformation of aromatic ketones and ketoesters with the non-conventional yeast Pichia glucozyma
Contente, Martina Letizia,Molinari, Francesco,Zambelli, Paolo,De Vitis, Valerio,Gandolfi, Raffaella,Pinto, Andrea,Romano, Diego
, p. 7051 - 7053 (2014)
The non-conventional yeast Pichia glucozyma CBS 5766 has been used for the biotransformation of different aromatic ketones and ketoesters. The growth and biotransformation conditions were optimised for the reduction of acetophenone and under optimised conditions, propiophenone, butyrophenone and valerophenone were reduced to the corresponding (S)-alcohols with high yields and enantioselectivity. Ketoreductase(s) of Pichia glucozyma showed high catalytic activities also towards aromatic β- and γ-ketoesters, being often competitive with esterase(s). These concurrent activities allowed for the preparation of hydroxyesters, hydroxyacids and lactones often in a very selective manner.
Bakers' yeast reduction of γ and δ ketonitriles: Intermediates for the synthesis of (S)-5-hexanolide and other chiral lactones
Gopalan,Lucero,Jacobs,Berryman
, p. 1321 - 1329 (1991)
A number of γ and δ ketonitriles have been synthesized and their reduction with bakers' yeast carefully studied. Both 4-oxopentanenitrile and 5-oxohexanenitrile are reduced in moderate yields to the corresponding (S) alcohols of high ee while other substrates gave products of varying optical purities. These alcohols are useful intermediates for the preparation of chiral lactones, including the synthetically important (S)(-)-4-methylbutyrolactone and (S)-5-hexanolide.
A convenient route to optically active γ-substituted γ-lactones
Karnik, Anil V.,Patil, Sudhir T.,Patnekar, Subodh S.,Semwal, Abha
, p. 1420 - 1422 (2004)
Sodium borohydride reduction of 4-substituted (-)-menthyl/ (-)-bornyl-4-oxobutanoates followed by simple trituration in acidic medium at low temperature resulted in the formation of optically active γ-substituted γ-lactones.
Efficient intramolecular asymmetric reductions of α-, β-, and γ-keto acids with diisopinocampheylborane1
Veeraraghavan Ramachandran,Brown, Herbert C.,Pitre, Sangeeta
, p. 17 - 18 (2001)
(equation presented) α-, β-, and γ-Keto acids are reduced with diisopinocampheylborane at room temperature to the corresponding hydroxy acids with predictable stereochemistry in very high ee. The γ-hydroxy acids produced were conveniently cyclized to the corresponding lactones. This provides a simple synthesis of 4-hexanolide, a component of the pheromone secreted by the female dermestid beetle Trogoderma glabrum.
Nickel-Catalyzed Asymmetric Hydrogenation of γ-Keto Acids, Esters, and Amides to Chiral γ-Lactones and γ-Hydroxy Acid Derivatives
Guo, Qianling,Hou, Guohua,Huang, Yuping,Xiao, Guiying,Xie, Chaochao,Zi, Guofu
supporting information, p. 2722 - 2727 (2022/04/19)
A highly efficient asymmetric hydrogenation of a series of γ-keto acid derivatives, including γ-keto acids, esters, and amides, using a Ni-(R,R)-QuinoxP? complex as the catalyst has been developed to afford chiral γ-hydroxy acid derivatives with excellent enantioselectivities, up to 99.9% ee. This method provides not only an economical one-pot approach for the synthesis of chiral γ-lactones but also access to (S)-norfluoxetine, an inhibitor of neural serotonin reuptake and an essential intermediate for pharmaceutical synthesis.
Method for asymmetrically synthesizing dihydrofuran-2-(3H)-one compound under catalysis of nickel
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Paragraph 0023-0042, (2021/08/07)
The invention relates to a method for asymmetrically synthesizing a dihydrofuran-2-(3H)-one compound under the catalysis of nickel, wherein the method comprises the steps: by taking gamma-ketonic acid as a raw material, adding a nickel catalyst, a ligand
Synthesis of chiral γ-lactones via a RuPHOX-Ru catalyzed asymmetric hydrogenation of aroylacrylic acids
Lu, Yufei,Li, Jing,Zhu, Yue,Shen, Jiefeng,Liu, Delong,Zhang, Wanbin
supporting information, p. 3643 - 3649 (2019/05/29)
An asymmetric hydrogenation of aroylacrylic acids catalyzed by RuPHOX-Ru catalyst has been developed, affording the corresponding chiral γ-lactones in high yields and with up to 93% ee. The methodology has the advantage of utilizing easily accessible substrates and has therefore expand the scope of the resulting chiral γ-lactones. Furthermore, high catalytic efficiency was achieved in that the reduction of both the C[dbnd]C and C[dbnd]O double bonds was achieved in one step. The current work provides an alternative and convenient pathway for the synthesis of a wide range of chiral γ-lactones.
