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Conformationally Rigid Chiral Pyridine N ‐Oxides as Organocatalyst: Asymmetric Allylation of Aldehydes
Author(s) -
Gnanamani Elumalai,
Someshwar Nagamalla,
Ramanathan Chinnasamy Ramaraj
Publication year - 2012
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201200115
Subject(s) - chemistry , pyridine , yield (engineering) , chloroform , pyridine n oxide , base (topology) , lewis acids and bases , organic chemistry , catalysis , enantioselective synthesis , oxide , medicinal chemistry , mathematical analysis , materials science , mathematics , metallurgy
A pyridine unit with a conformationally rigid chiral backbone has been designed and synthesized in an enantiomerically pure form to utilize in the Lewis base‐catalyzed Sakurai–Hosomi–Denmark‐type allylation reaction. The chiral pyridine N ‐oxide in 1:1 mixture of chloroform and 1,1,2,2‐tetrachloroethane produced the homoallylic alcohols in up to 98% yield and up to 94% ee .