The efficient enantiodivergence of (dl)-1,3-diacetyl-2- imidazolidinethiones by enantioselective catalytic deacetylation

Tetrahedron Letters

Volumn 40, Issue 34, 1999, Pages 6285-6288

  Yokoyama, Kazuhiro ^a   Ishizuka, Tadao ^a   Kunieda, Takehisa ^a  

^a KUMAMOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 DIACETYL 2 IMIDAZOLIDINETHIONE DERIVATIVE; AMINOALCOHOL; BORANE DERIVATIVE; IMIDAZOLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; DEACETYLATION; KINETICS; NONHUMAN; STEREOCHEMISTRY;

EID: 0033588060     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01277-0     Document Type: Article

References (19)

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13. 11)
14. 3) δ:0.59 (3H, s), 2.15 (3H, br), 3.33 (1H, dd, J = 3.1, 7.9 Hz), 3.85 (1H, dd, J = 3.1, 7.9 Hz), 4.18 (1H, d, J = 3.1 Hz), 4.42 (1H, d, J = 3.1 Hz), 7.00-7.40 (8H, m).
15. 3 · THF (1.2 mmol) in THF was added dropwise to this mixture over a period of 30 min, followed by stirring at 10 °C for an additional 30 min. Acidification with a 2N-HCl solution, followed by the usual work-up gave (R, R)-7b (>99% ee) in 34%, and (R, R)-8b (93% ee) in 165%, and (S, S)-9b (94% ee) in 48% yields. The optical purity was determined as the 1,3-diacetates by HPLC analysis on a Chiralcel OD-H column.
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