Publication Type
Publication Type
Peer Reviewed Journal
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Authors
Schanz, HJ; Linseis, MA; Gilheany, DG; ;
Year
2003
Month
March
Journal
Tetrahedron Asymmetry
Title
Improved resolution methods for (R,R)- and (S,S)-cyclohexane-1,2-diamine and (R)- and (S)-BINOL
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Published
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Volume
14
Issue
18
Start Page
2763
End Page
2769
Abstract
Starting from inexpensive L-(+)-tartaric acid, it was possible to resolve and obtain pure both enantiomers of trans-cyclohexane-1,2-diamine 1 and thence both enantiomers of BINOL 2, two of the most powerful, chiral inducing backbones in asymmetric catalysis. The modified method is very economic, not only due to an almost doubling of the overall yields of enantiomerically pure compounds (86% 1, 83% 2) but also due to the easy recovery of resolving agent 1 [66% (R,R)-1, 79% (S,S)-1] in the BINOL resolution. An improvement in the yield of the preparation of racemic BINOL is also recorded, (C) 2003 Elsevier Ltd. All rights reserved..
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