Stereoselective formation of N-acyliminium ion via chiral N,O-acetal TMS ether and its application to the synthesis of beta-amino acids |
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Authors: | Shin Dong-Yun Jung Jae-Kyung Seo Seung-Yong Lee Yong-Sil Paek Seung-Mann Chung Young Keun Shin Dong Mok Suh Young-Ger |
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Affiliation: | College of Pharmacy, Seoul National University, Seoul 151-742, Korea. |
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Abstract: | [reaction: see text] The highly stereoselective synthesis of beta-amino acids via the chiral 4-phenyloxazolidinone-controlled linear N-acyliminium ion reaction has been achieved by employing chiral N,O-acetal TMS ethers. In addition, the mechanism of the excellent stereochemical outcome has been elucidated. The oxazolidinone auxiliary plays a dual role in stereocontrol: the E/Z geometry control of the N-acyliminium ion induced by an initial stereoselective amide reduction, leading to the chiral N,O-acetal TMS ether, and face control of the nucleophile attack in the N-acyliminium ion reaction. |
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