Stereoselective synthesis of 4-hydroxy-2-phenylproline framework |
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| Authors: | Kenji Maeda Ross A. Miller Ali Shafiee Joseph D. Armstrong III |
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| Affiliation: | a Process Research, Process R&D, Banyu Pharmaceutical Co., Ltd, 9-1 Kamimutsuna 3-chome, Okazaki, Aichi 444-0858, Japan
b Department of Process Research, Merck & Co., Inc. PO Box 2000, Rahway, NJ 07065, USA |
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| Abstract: | Highly diastereoselective (>20:1) bromo-lactonization of N-sulfonyl-2-allyl-2-phenylglycine methyl ester (11) was observed. Successive treatment of the chiral lactone with MeONa gave the desired (2S,4R)-4-hydroxy-2-phenylproline derivative in high yield without erosion of the diastereoselectivity. The starting chiral non-racemic compound (5) was prepared from the racemic 2-phenylglycine using a classical kinetic resolution (crystallization), an asymmetric phase transfer alkylation, and an enzyme-catalyzed kinetic resolution. |
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| Keywords: | 4-Hydroxyproline Optical resolution Phase transfer reaction Iodo cyclization Halo lactonization |
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