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Synthesis of Arylglycine and Mandelic Acid Derivatives through Carboxylations of α-Amido and α-Acetoxy Stannanes with Carbon Dioxide
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- Tsuyoshi Mita
- Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan
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- Masumi Sugawara
- Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan
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- Hiroyuki Hasegawa
- Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan
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- Yoshihiro Sato
- Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan
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Description
Incorporation reactions of carbon dioxide (CO(2)) with N-Boc-α-amido and α-acetoxy stannanes were developed using CsF as a mild tin activator. Monoprotected α-amido stannanes could be used, and the corresponding arylglycine derivatives were obtained in moderate-to-high yields under 1 MPa (10 atm) of CO(2) pressure. α-Acetoxy stannanes also underwent carboxylation to afford mandelic acid derivatives in excellent yields under ambient CO(2) pressure. Both transformations enabled the synthesis of α-tertiary and α-quaternary carboxylic acid derivatives. In addition, the chirality of (S)-N-tert-butylsulfonyl-α-amido stannanes was transferred with up to 90% inversion of configuration at 100 °C.
Journal
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- The Journal of Organic Chemistry
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The Journal of Organic Chemistry 77 (5), 2159-2168, 2012-02-14
American Chemical Society (ACS)
