TY - JOUR
T1 - 3-Mono-Substituted BINOL Phosphoric Acids as Effective Organocatalysts in Direct Enantioselective Friedel–Crafts-Type Alkylation of N-Unprotected α-Ketiminoester
AU - Yonesaki, Ryohei
AU - Kondo, Yuta
AU - Akkad, Walaa
AU - Sawa, Masanao
AU - Morisaki, Kazuhiro
AU - Morimoto, Hiroyuki
AU - Ohshima, Takashi
N1 - Funding Information:
This work was supported by Grant-in-Aid for Scientific Research on Innovative Areas (JSPS KAKENHI Grant Number JP15H05846 in Middle Molecular Strategy for T.O.) and Grant-in-Aid for Scientific Research (B) (JSPS KAKENHI Grant Number JP17H03972 for T.O.) and (C) (JSPS KAKENHI Grant Numbers JP15K07860 and JP18K06581 for H.M.) from JSPS, Basis for Supporting Innovative Drug Discovery and Life Science Research (BINDS) (Grant Number JP17am0101091) from AMED, Takeda Science Foundation, Uehara Memorial Foundation and the Tokyo Biochemical Research Foundation. R.Y., M.S., and K.M. thank JSPS for Research Fellowships for Young Scientists. The computation was mainly carried out using the computer facilities at Research Institute for Information Technology, Kyushu University. We thank Prof. Go Hirai's group for the use of a polarimeter.
Funding Information:
This work was supported by Grant-in-Aid for Scientific Research on Innovative Areas (JSPS KAKENHI Grant Number JP15H05846 in Middle Molecular Strategy for T.O.) and Grant-in-Aid for Scientific Research (B) (JSPS KAKENHI Grant Number JP17H03972 for T.O.) and (C) (JSPS KAKENHI Grant Numbers JP15K07860 and JP18K06581 for H.M.) from JSPS, Basis for Supporting Innovative Drug Discovery and Life Science Research (BINDS) (Grant Number JP17am0101091) from AMED, Takeda Science Foundation, Uehara Memorial Foundation and the Tokyo Biochemical Research Foundation. R.Y., M.S., and K.M. thank JSPS for Research Fellowships for Young Scientists. The computation was mainly carried out using the computer facilities at Research Institute for Information Technology, Kyushu University. We thank Prof. Go Hirai’s group for the use of a polarimeter.
Publisher Copyright:
© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
PY - 2018/10/12
Y1 - 2018/10/12
N2 - Although BINOL-derived phosphoric acids are among the most widely used chiral Brønsted acid organocatalysts, their structures are mostly limited to 3,3′-disubstituted ones and simple 3-mono-substituted ones without any polar functionalities on the 3-substituent have not been used in highly enantioselective reactions. This work reports such 3-mono-substituted analogues as effective organocatalysts in direct highly enantioselective Friedel–Crafts-type alkylation of N-unprotected α-ketiminoester. The origin of the observed high enantioselectivity with the 3-mono-substituted catalyst is also discussed.
AB - Although BINOL-derived phosphoric acids are among the most widely used chiral Brønsted acid organocatalysts, their structures are mostly limited to 3,3′-disubstituted ones and simple 3-mono-substituted ones without any polar functionalities on the 3-substituent have not been used in highly enantioselective reactions. This work reports such 3-mono-substituted analogues as effective organocatalysts in direct highly enantioselective Friedel–Crafts-type alkylation of N-unprotected α-ketiminoester. The origin of the observed high enantioselectivity with the 3-mono-substituted catalyst is also discussed.
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U2 - 10.1002/chem.201804078
DO - 10.1002/chem.201804078
M3 - Article
C2 - 30098059
AN - SCOPUS:85052985511
SN - 0947-6539
VL - 24
SP - 15211
EP - 15214
JO - Chemistry - A European Journal
JF - Chemistry - A European Journal
IS - 57
ER -