Improved practical asymmetric synthesis of α-alkylmandelic acids utilizing highly diastereoselective alkylation of 5-aryl-2-(1-naphthyl)-1,3- dioxolan-4-ones

Organic Process Research and Development

Volumn 10, Issue 3, 2006, Pages 500-504

  Misaki, Tomonori ^a   Ureshino, Satoko ^a   Nagase, Ryohei ^a   Oguni, Yumiko ^a   Tanabe, Yoo ^a  

^a KWANSEI GAKUIN UNIVERSITY   (Japan)

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EID: 33745762715     PISSN: 10836160     EISSN: None     Source Type: Journal    
DOI: 10.1021/op050263j     Document Type: Article

References (40)

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35. Intermediates 6, 7, and 7′ were not be isolable, due to the thermal instability. Private communication from the Banyu group: A careful technique of azeotropic removal of i-PrOH under reduced pressure at low temperature was required to generate intermediate 6.
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40. Probably because intermediary 1-naphthylmethylinum cation was generated more smoothly than tert-butylmethylinium cation, 1-naphthaldehyde underwent rapid and safe acetal formation to give 9.