Regio- and Stereoselective (SN2) N-, O-, C- and S-Alkylation Using Trialkyl Phosphates
Amit Banerjee*, Tomohiro Hattori*, Hisashi Yamamoto*
*Molecular Catalyst Research Center, Chubu University, Kasugai, Aichi 487-8501, Japan,
Email: banerjeeam07isc.chubu.ac.jp, thattori
isc.chubu.ac.jp,
hyamamoto
isc.chubu.ac.jp
A. Banerjee, T. Hattori, H. Yamamoto, Synthesis, 2023, 55, 315-332.
DOI: 10.1055/a-1504-8366
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Abstract
Trialkyl phosphates are inexpensive and stable at room temperature, under air, and are easy to handle. Mild, straightforward and powerful methods for nucleophilic alkylation of various N-, O-, C- and S-nucleophiles using readily available trialkyl phosphates proceed smoothly in excellent yields. Stereoselective transfer of secondary alkyl groups have also been achieved with inversion of configuration.
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Key Words
trialkyl phosphates, stereoselectivity, SN2 reaction, amides (N-alkylation, C-alkylation), secondary alkylation, vinyl ethers
ID: J66-Y2023