Synthesis p. 2507 - 2510 (2003)
Update date:2022-07-29
Topics: Synthesis THF organic layer Hydrolysis Na2CO3 Reagent Compound
Periasamy, Mariappan
Seenivasaperumal, Muthu
Rao, Vutukuri Dharma
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)-(-)-α,α-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 C2-symmetric (2S,5S)-2,5-diphenylpyrrolidine derivatives 3a-e (45 to 75% yield) via the corresponding dimesylate prepared using MsCl and Et3N.
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