Chemoenzymatic total synthesis and determination of the absolute configuration of (S)-nebracetam

Tetrahedron Asymmetry

Volumn 19, Issue 18, 2008, Pages 2115-2118

  Yamashita, Sho ^a   Mase, Nobuyuki ^a   Takabe, Kunihiko ^a  

^a SHIZUOKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

LACTAM DERIVATIVE; NEBRACETAM; NITROMETHANE; TRIACYLGLYCEROL LIPASE;

ARTICLE; CATALYSIS; CHIRALITY; CRYSTALLIZATION; ENZYME SYNTHESIS; MICHAEL ADDITION; PRIORITY JOURNAL; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 53749089095     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2008.09.004     Document Type: Article

References (18)

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8. We tried to lower the reaction temperature to -25 °C, but low chemical yield (45%) and no improvement in diastereoselectivity were observed after 2 d stirring. Other organic amine base such as N,N-diisopropylethylamine was not efficient, and no reaction was observed. Michael addition of 2-nitropropane to 9d gave the Micheal product in 95% yield as a single diastereomer.
9. Takabe K., Suzuki M., Nishi T., Hiyoshi M., Takamori Y., Yoda H., and Mase N. Tetrahedron Lett. 41 (2000) 9859-9863
10. R = 33.41 (R-isomer), 43.35 (S-isomer) min.
11. R = 17.06 (R-isomer), 13.19 (S-isomer) min.
12. R = 47.37 (R,R-isomer), 53.07 (S,R-isomer) 64.99 (S,S-isomer), 70.85 (R,S-isomer) min.
13. Karplus M. J. Am. Chem. Soc. 85 (1963) 2870-2871
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15. R = 20.08 (trans-isomer), 26.81 (cis-isomer) min.
16. R = 56.30 (R-isomer), 62.12 (S-isomer) min.
17. 2), 33.96 (CH).
18. 3).