期刊
SYNTHESIS-STUTTGART
卷 -, 期 16, 页码 2507-2510出版社
GEORG THIEME VERLAG KG
DOI: 10.1055/s-2003-42447
关键词
asymmetric reduction; chiral 1,4-diols; chiral pyrrolidine derivatives; 1,4-dione
Asymmetric reduction of 1,4-diphenylbutane-1,4-dione (1) was carried out using the reducing agents NaBH4, BH3.THF, and PhNEt2.BH3 in combination with the chiral reagents (S)-(-)-alpha,alpha-diphenyl-2-pyrrolidinemethanol (4) or (S)-proline (5), in the presence of TMSCl or B(OMe)(3) under various conditions to obtain the corresponding 1.4-diol 2 in 52% to 97% ee. The chiral 1,4-diol 2 was converted to various C-2-symmetric (2S,5S)-2,5-diphenyl-pyrrolidine derivatives 3a-e (45 to 75% yield) via the corresponding dimesylate prepared using MsCl and Et3N.
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