Premium
Organoboranes for synthesis. 18. C 2 ‐symmetric α,α′‐disubstituted‐2,6‐pyridinedimethanols as catalytic chiral ligands for the enantioselective nucleophilic addition of diethylzinc to aldehydes
Author(s) -
Brown Herbert C.,
Chen GuangMing,
Ramachandran P. Veeraraghavan
Publication year - 1997
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/(sici)1520-636x(1997)9:5/6<506::aid-chir17>3.0.co;2-s
Subject(s) - diethylzinc , chemistry , enantioselective synthesis , steric effects , benzaldehyde , nucleophile , chirality (physics) , nucleophilic addition , ligand (biochemistry) , catalysis , electronic effect , chiral auxiliary , medicinal chemistry , stereochemistry , combinatorial chemistry , organic chemistry , biochemistry , nambu–jona lasinio model , chiral symmetry breaking , physics , receptor , quantum mechanics , quark
Several new chiral auxiliaries with differing steric and electronic environments, such as α,α′‐dimethyl‐2,6‐pyridinedimethanol, α,α′‐ditrifluoromethyl‐2,6‐pyridinedimethanol, α,α′‐dipentafluoroethyl‐2,6‐pyridinedimethanol, and α,α′‐diallyl‐2,6‐pyridinedimethanol, have been examined and compared with α,α′‐di‐ t ‐butyl‐2,6‐pyridinedimethanol for their ability to control the enantioselective addition of diethylzinc to benzaldehyde. The best chiral ligand has been tested for other representative aldehydes with varying steric and electronic requirements. The product alcohols are obtained in 21–78% ee. Chirality 9:506–511, 1997. © 1997 Wiley‐Liss, Inc.