Download PDF
Synfacts 2015; 11(2): 0207
DOI: 10.1055/s-0034-1379762
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

Asymmetric Conjugate Addition of ArB(OH)2 to Enones with Chiral Rh-POF

Contributor(s):
Yasuhiro Uozumi
,
Takao Osako
Dong J, Liu Y, * Cui Y. * Shanghai Jiao Tong University and Collaborative Innovation Center of Chemical Science and Engineering, Tianjin, P. R. of China
Chiral Porous Organic Frameworks for Asymmetric Heterogeneous Catalysis and Gas Chromatographic Separation.

Chem. Commun. 2014;
50: 14949-14952
CrossrefGoogle Scholar
Further Information

Publication History

Publication Date:
19 January 2015 (online)

 
 PDF Download Permissions and Reprints

Key words

porous organic framework - conjugate addition - rhodium - enones - arylboronic acids

Significance

A rhodium complex supported on a chiral porous organic framework (chiral POF-Rh) was prepared by the Suzuki–Miyaura coupling of chiral bistriflate 1 and 2, followed by the complexation with [Rh(C2H4)2Cl]2 (eq 1). Chiral POF-Rh catalyzed the asymmetric conjugate addition of arylboronic acids to enones to give the corresponding 1,4-addition products in up to 93% yield with up to 93% ee (15 examples, eq. 2).


#

Comment

Chiral POF and chiral POF-Rh were characterized by NMR, BET, TEM, SEM, TGA, ­PXRD, and ICP analyses. In the reaction of phenylboronic acid with 2-cyclohexenone, chiral POF was recovered by centrifugation and reused by treatment with [Rh(C2H4)2Cl]2 without significant loss of activity and enantioselectivity (5th recycling run: 87% yield, 84% ee).


#
#


   Permissions and Reprints