Factors affecting the efficiency and stereoselectivity of α-amino acid synthesis by the Petasis reaction |
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Authors: | Timothy J Southwood Craig A Hutton |
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Institution: | a School of Chemistry, The University of Sydney, Sydney, NSW 2006, Australia b School of Chemistry, The University of Melbourne, Melbourne, VIC 3010, Australia c Bio21 Molecular Science and Biotechnology Institute, The University of Melbourne, Melbourne, VIC 3010, Australia |
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Abstract: | The use of chiral secondary amines containing only one branched substituent has been shown to give optimal yields and stereoselectivities in the preparation of α-amino acids using the Petasis reaction. While the use of chiral primary amines generally gives products in low to moderate diastereoselectivity, chiral secondary amines generally give products in >95:5 diastereoselectivity. Additionally, the use of amines with two chiral (and by definition, branched) N-alkyl substituents results in significantly reduced yields with respect to to secondary amines with one or no branched N-alkyl substituents. |
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Keywords: | Amino acids Petasis reaction Multi-component coupling Boronic acid Mannich reaction |
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