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Synfacts 2008(11): 1229-1229  
DOI: 10.1055/s-0028-1083393
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Asymmetric Allylic Substitution in Water with a Polymeric Pd Catalyst

Contributor(s): Yasuhiro Uozumi, Yoichi M. A. Yamada, Toshihiro Watanabe
Y. Uozumi*, H. Takenaka, T. Suzuka
Institute for Molecular Science (IMS) and CREST, Okazaki, Japan
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Publication History

Publication Date:
23 October 2008 (online)

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Significance

Asymmetric π-allylic substitution of meso-1,4-diacetoxycycloalkenes was performed with an amphiphilic PS-PEG resin-supported chiral phosphine-palladium complex. Thus, the reaction of cis-1,4-diacetoxycyclopentene (meso-1) with diethyl malonate, dibenzylamine and phenols in water gave the corresponding 1-acetoxy-4-substituted cyclopentenes 2a-i with 90-99% ee in 43-64% yield. Cyclohexenyl ester (meso-4) also underwent etherification with phenol to give 5 in 37% yield (95% ee) and 11% of 6.