Utilization of Aminophosphonates in the Petasis Boronic Acid Mannich Reaction

Abstract Aminophosphonates were used as amine components in the Petasis boronic acid Mannich reaction. With the use of α-aminophosphonates, several N-phosphonomethylglycine derivatives were prepared in modest to good yields and high diastereoselectivities. The method affords the possibility of varia...

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Bibliographic Details
Published in:Synlett 2010, Vol.2010 (1), p.73-76
Main Authors: Shevchuk, Michael V., Sorochinsky, Alexander E., Khilya, Volodymyr P., Romanenko, Vadim D., Kukhar, Valery P.
Format: Article
Language:English
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Summary:Abstract Aminophosphonates were used as amine components in the Petasis boronic acid Mannich reaction. With the use of α-aminophosphonates, several N-phosphonomethylglycine derivatives were prepared in modest to good yields and high diastereoselectivities. The method affords the possibility of variation for the substituents in the position α to the phosphorus and nitrogen atoms. By using the same methodology, highly functionalized amino acids were prepared starting from (R)-β-amino-α,α-difluoromethylphosphonate.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-0029-1218386