Highly enantioselective synthesis of 1,3-mercaptoalcohols from α,β- unsaturated ketones: Asymmetric bifunctional group exchange reaction

Tetrahedron Letters

Volumn 41, Issue 18, 2000, Pages 3437-3441

  Shiraki, Hiroaki ^a   Nishide, Kiyoharu ^a   Node, Manabu ^a  

^a KYOTO PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 MERCAPTO ALCOHOL DERIVATIVE; ALCOHOL DERIVATIVE; CHALCONE DERIVATIVE; KETONE DERIVATIVE; REAGENT; UNCLASSIFIED DRUG;

ARTICLE; ENANTIOMER; REACTION ANALYSIS; REDUCTION; SYNTHESIS;

EID: 0034728896     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00395-6     Document Type: Article

References (44)

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29. 2 in 17% yield, along with the other diastereomers.
30. The absolute configurations of the thiolic carbon in 3c-f were determined by NOE experiments, because a 1,3-mercapto alcohol formed a chair conformation of a six-membered ring by intramolecular hydrogen bonding between the oxygen atom and the hydrogen atom of the thiol.
31. 2 (37 mg, 0.18 mmol) was added dropwise dimethylaluminum chloride (1.0 M hexane solution, 0.21 ml, 0.22 mmol). After the mixture was stirred for 15 min at room temperature, a benzene solution (2 ml) of the α,β-unsaturated ketone 1c (75 mg, 0.36 mmol) was added, and the resulting mixture was stirred for 48 h at the same temperature. The reaction mixture was quenched with a 1N-HCl solution, and the aqueous layer extracted with chloroform. After the usual work-up, the product 2c (36 mg, 60%) was isolated by silica gel chromatography. A mixture of 2c (28 mg, 0.07 mmol), DBU (0.047 ml, 0.34 mmol), and benzyl mercaptan (15 μl, 0.13 mmol) in toluene (8 ml) was refluxed for 18 h. The usual work-up and purification by silica gel chromatography gave the 1,3-mercapto alcohol 3c (16 mg, 97% yield), along with 5 (18 mg, 91% yield).
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