Enantioselective 6- endo-trig Wacker-type cyclization of 2-geranylphenols: application to a facile synthesis of (−)-cordiachromene

An enantioselective intramolecular oxidative cyclization of 2-geranylphenols catalyzed by a Pd(II)-spiro bis(isoxazoline) complex is reported. The reaction proceeds in a 6- endo-trig manner to give chromene derivatives in reasonable yields and with moderate enantioselectivities. This transformation...

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Bibliographic Details
Published in:Tetrahedron: asymmetry 2010-04, Vol.21 (7), p.767-770
Main Authors: Takenaka, Kazuhiro, Tanigaki, Yugo, Patil, Mahesh L., Rao, C.V. Laxman, Takizawa, Shinobu, Suzuki, Takeyuki, Sasai, Hiroaki
Format: Article
Language:English
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Summary:An enantioselective intramolecular oxidative cyclization of 2-geranylphenols catalyzed by a Pd(II)-spiro bis(isoxazoline) complex is reported. The reaction proceeds in a 6- endo-trig manner to give chromene derivatives in reasonable yields and with moderate enantioselectivities. This transformation can be applied to a protecting-group-free total synthesis of naturally occurring cordiachromene.
ISSN:0957-4166
1362-511X
DOI:10.1016/j.tetasy.2010.04.060