Deracemization of acyclic α-hydroxy ketone derivatives by dynamic resolution using an optically active host compound

Synlett

Volumn , Issue 5, 2007, Pages 729-732

  Matsumoto, Kazutsugu ^a   Otsuka, Keiko ^a   Okamoto, Tomomi ^a   Mogi, Hideto ^a  

^a MEISEI UNIVERSITY   (Japan)

Author keywords

Acyclic ketones; Deracemization; Enantiomeric resolution; Host guest systems; Optically active compounds

Indexed keywords

ACYCLIC ALPHA HYDROXY KETONE DERIVATIVE; KETONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; ENANTIOMER; ENANTIOSELECTIVITY; OPTICS; RACEMIZATION;

EID: 33947730535     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-970770     Document Type: Article

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42. 3), S-form.
43. R = 40 (R) and 50 (S) min.
44. The deracemization did not occur for the reactions using the other TADDOL derivatives bearing a cyclopentane ring and a dimethyl group [(-)-2,2-tetramethylene- and 2,2-dimethyl-α,α,α′, α′-tetraphenyl-l,3-dioxolan-4,5-dimethanol, respectively], (+)-1,1′-bi-2-naphthol, and (-)-hydrobenzoin as chiral host compounds under the same conditions.
45. Although the ee of (S)-1 increased according to the extension of the reaction time (42% ee for one day), the reaction for over three days gave almost the same result as that of the three-day reaction. We then decided that the racemizations in all cases were carried out for three days.
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48. 13
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