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Synthesis of N ‐squaramidoacids and their application in asymmetric borane reduction of prochiral ketones
Author(s) -
Zhang Ji,
Li LeiLei,
Zou HaiHua,
Chen JunJun,
Yu KaiBei,
Xie RuGang
Publication year - 2004
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.20040220618
Subject(s) - chemistry , borane , enantiomer , ligand (biochemistry) , catalysis , proline , enantiomeric excess , reduction (mathematics) , enantioselective synthesis , sulfonyl , organic chemistry , alcohol , chiral ligand , amino acid , combinatorial chemistry , medicinal chemistry , stereochemistry , receptor , biochemistry , alkyl , geometry , mathematics
A series of novel N ‐squaramidoacid ligands were prepared conveniently. Without converting to corresponding amino alcohols, these ligands could be used in asymmetric borane reduction of prochiral aromatic ketones to give secondary alcohols in good to excellent enantiomeric excesses. The results showed that N ‐squaramidoacids are more efficient ligands than N ‐sulfonyl amino acids. N ‐Squaryl proline was proved to be an excellent ligand in this catalytic asymmetric process.