Download PDF
Synfacts 2014; 10(8): 0828
DOI: 10.1055/s-0034-1378424
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Asymmetric Ring Opening of Oxabenzonorbornadienes with Amines

Contributor(s):
Hisashi Yamamoto
,
Wafa Gati
Luo R, * Xie L, Liao J, Xin H, Chan AS. C. Gannan Medical University, Jiangxi and Hong Kong Baptist University, P. R. of China
Tunable Chiral Monophosphines as Ligands in Enantioselective Rhodium-Catalyzed Ring Opening of Oxabenzonorbornadienes with Amines.

Tetrahedron: Asymmetry 2014;
25: 709-717
CrossrefSearch in Google Scholar
Further Information

Publication History

Publication Date:
18 July 2014 (online)

 
 PDF Download Permissions and Reprints

Key words

rhodium - chiral monophosphines - ring opening - oxabenzonorborna-dienes

Significance

The authors present an efficient asymmetric rhodium-catalyzed ring opening of ­oxabenzonorbornadienes with amines using new tunable chiral monophosphines as ligands. This new method leads to the formation of a series of dihydronaphthalenes in high yields and enantio­selectivities.


#

Comment

Chiral phosphorus ligands are synthesized in order to study their efficiency in the asymmetric ring opening of oxabenzonorbornadienes with amines. An intensive screening of reaction conditions (rhodium catalyst, additive, ligand, solvent, temperature) was reported to establish optimized reaction conditions, giving access to a wild range of dihydronaphthalenes in high yields (up to 97%) and high to excellent enantioselectivities (>99%) in addition to a wild tolerance for cyclic and acyclic amines.


#
#


   Permissions and Reprints