Practical synthesis of optically active styrene oxides via reductive transformation of 2-chloroacetophenones with chiral rhodium catalysts

Organic Letters

Volumn 4, Issue 24, 2002, Pages 4373-4376

  Hamada, Takayuki ^a   Torii, Takayoshi ^a   Izawa, Kunisuke ^a   Noyori, Ryoji ^b   Ikariya, Takao ^c  

^a AJINOMOTO CO INC   (Japan)

^b NAGOYA UNIVERSITY   (Japan)

^c TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

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ARTICLE;

EID: 0041736497     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol020213o     Document Type: Article

References (34)

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18. 5 in hexane) to give almost quantitatively 2-chlorophenylethanol 3a. The ee value was determined by HPLC analysis. See Supporting Information.
19. 2 and 0.5 mol % (R,R)-TsDPEN gave an 85% yield and 75% ee.
20. 2 and 0.5 mol % (R,R)-TsDPEN gave an 85% yield and 75% ee.
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30. One-Pot Procedure for Synthesis of 4a. A mixture of 2-chloroacetophenone 2a (5 mmol) and catalyst 1a (0.005 mmol) in a 5:2 mixture of formic acid to triethylamine (1.0 mL) and 2-propanol (6.0 mL) was stirred at 25°C for 2 h. The reaction mixture was then treated with 2 M NaOH aqueous solution (10.0 mL) at 0°C for 1 h. After the usual workup procedure, (R)-styrene oxide 4a with 96.8% ee was obtained in 83% yield. The ee value was determined by HPLC analysis. In a large-scale experiment. the reaction of 4.73 g of 2a with 1a (S/C = 5000) gave the corresponding optically active styrene oxide with 94% ee in a 93% total isolated yield (3.54 g). Even commercially available reagents and solvents without special purification could be used in this reaction.
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