@article{6405219c4b01432ba3108aa42623ee89,
title = "Double nucleophilic N-alkylation of α-oxime-esters with Grignard reagents",
abstract = "Double nucleophilic N-alkylation of α-oxime-esters, affording N,N-dialkyl-α-amino acids is herein described. Grignard reagents accomplished double N-alkylations via umpolung and various N,N-dialkylated α-amino acids were successfully synthesized in 15 min. Both electron-withdrawing sulfonyl groups and electron-donating silyl and methyl groups on oximes were available. Alkylmagnesium species and (E)-configuration of α-oxime-ester were essential to this cascade reaction.",
keywords = "Amino acid, Cascade reaction, Electrophilic amination, Oxime, Umpolung",
author = "Yusuke Mizutani and Hiroki Tanimoto and Tsumoru Morimoto and Yasuhiro Nishiyama and Kiyomi Kakiuchi",
note = "Funding Information: We are grateful for the support of this research from Otsuka Pharmaceutical Co. Award in Synthetic Organic Chemistry, Japan. We wish to acknowledge Kuraray Co., Ltd for the gift of 4-MTHP (4-methyltetrahydro-2H-pyran). We also thank Ms. Mika Yamamura and Ms. Yuriko Nishiyama for HRMS measurements and to Mr. Shohei Katao for X-ray crystallographic analysis. ",
year = "2012",
month = oct,
day = "31",
doi = "10.1016/j.tetlet.2012.08.091",
language = "英語",
volume = "53",
pages = "5903--5906",
journal = "Tetrahedron Letters",
issn = "0040-4039",
publisher = "Elsevier Ltd.",
number = "44",
}