Enantioselective synthesis utilizing enantiomorphous organic crystal of achiral benzils as a source of chirality in asymmetric autocatalysis

Organic Letters

Volumn 10, Issue 18, 2008, Pages 4085-4088

  Kawasaki, Tsuneomi ^a   Harada, Yuuki ^a   Suzuki, Kenta ^a   Tobita, Takayuki ^a   Florini, Nicola ^b   Pályi, Gyula ^b   Soai, Kenso ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

^b UNIVERSITY OF MODENA AND REGGIO EMILIA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

BENZIL; DRUG DERIVATIVE; PHENYLGLYOXAL; PYRIMIDINE; PYRIMIDINE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMISTRY; ENZYME SPECIFICITY; STEREOISOMERISM; SYNTHESIS;

CATALYSIS; PHENYLGLYOXAL; PYRIMIDINES; STEREOISOMERISM; SUBSTRATE SPECIFICITY;

EID: 55949120492     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol801600y     Document Type: Article

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67. The single crystal with enough size to perform the asymmetric autocatalysis using as the chiral initiator could not be obtained in the present stage. Thus, the powder (particle size: 10-20 μm) of 4,4′- dibromobenzil crystals used as chiral source of asymmetric autocatalysis was prepared by grinding the powder-like crystals of 2, which were grown by a seeding method under stirring conditions using the fragment of native single crystals whose absolute configuration was known by X-ray analysis (The details on the preparation of single and powder-like crystals of 2 are presented in the Supporting Information).
68. 2Zn (0.8 mmol, 0.8 mL, 1.0 M toluene solution) were added, a solution of 3 (75.3 mg, 0.4 mmol) in toluene (2.0 mL) was added dropwise over a period of 50 min at 0 °C. After the mixture was stirred for 2 h, the reaction was quenched with a mixture of 30% aqueous ammonia and saturated aqueous ammonium chloride (2:1, v/v) solution (10 mL). The mixture extracted using ethyl acetate three times. The combined organic layers were dried over anhydrous sodium sulfate and evaporated in vacuo. Purification of the residue by silica gel column chromatography (hexane/ethyl acetate, 3:1 to 2:1, v/v) gave the (R)-alkanol 4 (131.4 mg, 0.566 mmol, 96% ee) in 87% yield.