TY - JOUR
T1 - Effects of ring substituents on enantioselective recognition of amino alcohols and acids in uryl-based binol receptors
AU - Nandhakumar, Raju
AU - Ryu, Jayoung
AU - Park, Hyunjung
AU - Tang, Lijun
AU - Choi, Sujung
AU - Kim, Kwan Mook
N1 - Funding Information:
This work was supported by the Ministry of Science & Technology of Korea through NRL, SRC program of KOSEF (R11-2005-008-000000) and KRF (2024-005-C00093).
PY - 2008/8/11
Y1 - 2008/8/11
N2 - The uryl-based binol aldehyde, (S)-2-hydroxy-2′-(3-phenyluryl-benzyl)-1,1′-binaphthyl-3-carboxaldehyde (1), binds 1,2-amino alcohols and amino acids stereoselectively by reversible formation of imine bond. Hydrogen bond (between uryl group and alcohol -OH moiety) plays an important role in the stereoselectivity of amino alcohols. Hence, any substituents on phenyl group in 1 are expected to affect H-bond ability of uryl group. To study the effects of ring substituents on the stereoselective recognition of amino alcohols, (substituted phenyl)uryl-based chiral binol receptors have been prepared. The receptors with electron-donating X substituents have been synthesized from (S)-2-methoxymethoxy-2′-hydroxy-1,1′-binaphthyl-3-carboxaldehyde and X-phenyluryl-benzyl bromide. The receptors with electron-withdrawing Y substituents, however, required a different synthetic strategy including transformation of an aldehyde to alcohol. The incorporation of the electron withdrawing groups slightly accelerated the stereoselective recognition property of the receptor. Though the acceleration is not so remarkable, this work demonstrates the versatile derivatization of 1 in achieving higher stereoselective recognition of 1,2-amino alcohols and stereoconversion of l-amino acids to d-amino acids.
AB - The uryl-based binol aldehyde, (S)-2-hydroxy-2′-(3-phenyluryl-benzyl)-1,1′-binaphthyl-3-carboxaldehyde (1), binds 1,2-amino alcohols and amino acids stereoselectively by reversible formation of imine bond. Hydrogen bond (between uryl group and alcohol -OH moiety) plays an important role in the stereoselectivity of amino alcohols. Hence, any substituents on phenyl group in 1 are expected to affect H-bond ability of uryl group. To study the effects of ring substituents on the stereoselective recognition of amino alcohols, (substituted phenyl)uryl-based chiral binol receptors have been prepared. The receptors with electron-donating X substituents have been synthesized from (S)-2-methoxymethoxy-2′-hydroxy-1,1′-binaphthyl-3-carboxaldehyde and X-phenyluryl-benzyl bromide. The receptors with electron-withdrawing Y substituents, however, required a different synthetic strategy including transformation of an aldehyde to alcohol. The incorporation of the electron withdrawing groups slightly accelerated the stereoselective recognition property of the receptor. Though the acceleration is not so remarkable, this work demonstrates the versatile derivatization of 1 in achieving higher stereoselective recognition of 1,2-amino alcohols and stereoconversion of l-amino acids to d-amino acids.
KW - Electron-withdrawing group effect
KW - Stereoconversion
KW - Stereoselective recognition
UR - http://www.scopus.com/inward/record.url?scp=46149115357&partnerID=8YFLogxK
U2 - 10.1016/j.tet.2008.06.029
DO - 10.1016/j.tet.2008.06.029
M3 - Article
AN - SCOPUS:46149115357
VL - 64
SP - 7704
EP - 7708
JO - Tetrahedron
JF - Tetrahedron
SN - 0040-4020
IS - 33
ER -