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One‐Step Synthesis of Racemic α‐Amino Acids from Aldehydes, Amine Components, and Gaseous CO 2 by the Aid of a Bismetal Reagent
Author(s) -
Mita Tsuyoshi,
Higuchi Yuki,
Sato Yoshihiro
Publication year - 2013
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201202332
Subject(s) - stannane , reagent , chemistry , amine gas treating , amino acid , aldehyde , imine , organic chemistry , combinatorial chemistry , catalysis , biochemistry
Abstract α‐Amino acids are essential resources for human life and are highly useful as building blocks for organic synthesis. The core framework of an α‐amino acid can be divided into three basic components: an aldehyde, an amine, and carbon dioxide (CO 2 ). We report herein that a one‐step synthesis of α‐amino acids has been successfully achieved from these three basic and inexpensive chemicals with a single operation, in which the mixture of an aldehyde, a sulfonamide, and gaseous CO 2 was heated at 100 °C in the presence of Bu 3 Sn‐SnBu 3 and CsF. In this one‐pot sequential protocol, two important intermediates (imine and α‐amino stannane) are involved and the stannyl anion generated in situ plays a crucial role, particularly for the efficient stannylation of the imine in the presence of proton sources and for promoting retrostannylation of the undesired α‐alkoxy stannane owing to its high stability and tolerance of the presence of proton sources. This methodology enabled the synthesis of a wide range of racemic arylglycine derivatives in high yields.