Novel Borane Reduction of Ether‐Protected Aromatic Lactams.

Hu, Wan‐Ping; Tsai, Pei-Ching; Hsu, Ming-Kuan; Wang, Jhi-Joung

doi:10.1002/chin.200438151

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Grignard Reaction Of (+/2)-cis-6a With Phenylmagnesium Bromide1

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2007

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“…To our surprise, the reduction of (S;2R,5S)-(þ)-8 with excess LiAlH 4 was also failed and the partial degradation of (S;2R,5S)-(þ)-8 was observed. By replacing LiAlH 4 with BH 3 ÁTHF, 37 the reduction process has performed smoothly to give a white crystal after purification.…”

Section: Grignard Reaction Of (+/2)-cis-6a With Phenylmagnesium Bromidementioning

confidence: 99%

Facile synthetic route to enantiopure unsymmetric cis‐2,5‐disubstituted pyrrolidines

Wang

Chen

et al. 2007

Chirality

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The (+/-)-cis-5-arylcarbamoyl-2-ethoxycarbonylpyrrolidines 6a-g were firstly synthesized in 53-64% yields by using meso-diethyl-2,5-dibromoadipate 3 and (S)-(-)-1-phenylethylamine in three steps. The diastereomeric mixture (S;2S,5R)-(-)-7 and (S;2R,5S)-(+)-8 were prepared by the Grignard reaction and separated by a flash column chromatography in 29 and 52% yields. The absolute configurations of (+)-8 was confirmed by X-ray crystallographic analysis and the enantiopure pyrrolidines (2S,5R)-(-)-9/(2R,5S)-(+)-9 and (2S,5R)-(-)-10/(2R,5S)-(+)-10 were obtained in good yields.

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Section: Grignard Reaction Of (+/2)-cis-6a With Phenylmagnesium Bromidementioning

confidence: 99%