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Asymmetric Ring Opening of meso ‐Epoxides with Aromatic Amines Using ( R )‐(+)‐BINOL‐Sc(OTf) 3 ‐NMM Complex as an Efficient Catalyst
Author(s) -
More Ganesh V.,
Bhanage Bhalchandra M.
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201300818
Subject(s) - chemistry , aniline , catalysis , ring (chemistry) , enantioselective synthesis , reaction conditions , combinatorial chemistry , organic chemistry , medicinal chemistry , oxide , molecular sieve
This work reports the asymmetric ring‐opening reaction of meso ‐epoxides with aromatic amines by using the highly efficient in situ generated ( R )‐(+)‐BINOL‐Sc(OTf) 3 ‐ N ‐methylmorpholine complex. The asymmetric ring opening of cis ‐stilbene oxide with various substituted aromatic amines gave enantioenriched β‐amino alcohols in good yields and with excellent enantioselectivities when the reaction was conducted at 0 °C for 12 h. The reaction proceeded under mild conditions using simple and inexpensive starting materials such as ( R )‐(+)‐1,1′‐bi‐2‐naphthol [( R )‐(+)‐BINOL], meso ‐stilbene oxide, aniline derivatives, and 4 Å molecular sieves. This new and versatile catalytic system has competitive advantages such as short reaction times, no additives, and no expensive chiral ligands that require a multistep synthesis under harsh reaction conditions.