Asymmetric Synthesis of Chiral Tertiary Alcohols in High Enantiomeric Excess

Chiral tertiary α-hydroxyketones were synthesized with high enantiopurity by asymmetric decarboxylative chlorination and subsequent nucleophilic substitution. We recently reported the asymmetric decarboxylative chlorination of β-ketocarboxylic acids in the presence of a chiral primary amine catalyst to obtain α-chloroketones with high enantiopurity. Here, we found that nucleophilic substitution of the resulting α-chloroketones with tetrabutylammonium hydroxide yielded the corresponding α-hydroxyketones without loss of enantiopurity. The reaction proceeded smoothly even at a tertiary carbon. The proposed method would be useful for the preparation of chiral tertiary alcohols.

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Asymmetric synthesis of new γ-butenolides via organocatalyzed epoxidation of chalcones

Organic & Biomolecular Chemistry ◽

10.1039/c7ob00165g ◽

2017 ◽

Vol 15 (29) ◽

pp. 6098-6103 ◽

Cited By ~ 6

Author(s):

Lucas C. C. Vieira ◽

Bianca T. Matsuo ◽

Lorena S. R. Martelli ◽

Mayara Gall ◽

Marcio W. Paixão ◽

...

Keyword(s):

Asymmetric Synthesis ◽

Enantiomeric Excess ◽

Chromatographic Purification

A greener three-step sequence, with only one single chromatographic purification, afforded γ-butenolides in moderate overall yield and high enantiomeric excess.

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Pyrrolidines and piperidines bearing chiral tertiary alcohols by nickel-catalyzed enantioselective reductive cyclization of N-alkynones

Communications Chemistry ◽

10.1038/s42004-018-0092-1 ◽

2018 ◽

Vol 1 (1) ◽

Cited By ~ 9

Author(s):

Guodu Liu ◽

Wenzhen Fu ◽

Xingye Mu ◽

Ting Wu ◽

Ming Nie ◽

...

Keyword(s):

Reductive Cyclization ◽

Tertiary Alcohols ◽

Chiral Tertiary Alcohols

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Isolation of Rhodococcus sp. Strain ECU0066, a New Sulfide Monooxygenase-Producing Strain for Asymmetric Sulfoxidation

Applied and Environmental Microbiology ◽

10.1128/aem.01527-08 ◽

2008 ◽

Vol 75 (2) ◽

pp. 551-556 ◽

Cited By ~ 37

Author(s):

Ai-Tao Li ◽

Jian-Dong Zhang ◽

Jian-He Xu ◽

Wen-Ya Lu ◽

Guo-Qiang Lin

Keyword(s):

Enzyme Activity ◽

Asymmetric Synthesis ◽

Bacterial Strain ◽

Enantiomeric Excess ◽

Good Activity ◽

Rich Medium ◽

Practical Application ◽

Chiral Sulfoxides ◽

Good Potential ◽

Rhodococcus Sp

ABSTRACT A new and efficient sulfide monooxygenase-producing strain, ECU0066, was isolated and identified as a Rhodococcus sp. that could transform phenylmethyl sulfide (PMS) to (S)-sulfoxide with 99% enantiomeric excess via two steps of enantioselective oxidations. Its enzyme activity could be effectively induced by adding PMS or phenylmethyl sulfoxide (PMSO) directly to a rich medium at the early log phase (6 h) of fermentation, resulting in over 10-times-higher production of the enzyme. This bacterial strain also displayed fairly good activity and enantioselectivity toward seven other sulfides, indicating a good potential for practical application in asymmetric synthesis of chiral sulfoxides.

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