学術雑誌論文

学術雑誌論文

text

Chemical Science. 2021, 12(34), p. 11525-11537

An umpolung-enabled copper-catalysed regioselective hydroamination approach to α-amino acids

Royal Society of Chemistry

英語

text

2021-09-14

https://doi.org/10.1039/d1sc03692k

Nishino S., Miura M., Hirano K.. An umpolung-enabled copper-catalysed regioselective hydroamination approach to α-amino acids. Chemical Science 12, 11525 (2021); https://doi.org/10.1039/d1sc03692k.

A copper-catalysed regio- and stereoselective hydroamination of acrylates with hydrosilanes and hydroxylamines has been developed to afford the corresponding α-amino acids in good yields. The key to regioselectivity control is the use of hydroxylamine as an umpolung, electrophilic amination reagent. Additionally, a judicious choice of conditions involving the CsOPiv base and DTBM-dppbz ligand of remote steric hindrance enables the otherwise challenging C-N bond formation at the α position to the carbonyl. The point chirality at the β-position is successfully controlled by the Xyl-BINAP or DTBM-SEGPHOS chiral ligand with similarly remote steric bulkiness. The combination with the chiral auxiliary, (−)-8-phenylmenthol, also induces stereoselectivity at the α-position to form the optically active unnatural α-amino acids with two adjacent stereocentres.

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92610

An umpolung-enabled copper-catalysed regioselective hydroamination approach to α-amino acids

Royal Society of Chemistry

英語

2021-09-14

Chemical Science

12

34

11525

11537

https://doi.org/10.1039/d1sc03692k

https://hdl.handle.net/11094/92610