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Synfacts 2008(5): 0493-0493  
DOI: 10.1055/s-2008-1072646
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Enantioselective Allylic Etherification Using Novel Ferrocenyl Ligand

Contributor(s): Hisashi Yamamoto, Marina Naodovic
F. L. Lam, T. T.-L. Au-Yeung, F. Y. Kwong, Z. Zhou, K. Y. Wong, A. S. C. Chan*
The Hong Kong Polytechnic University, Kowloon, Hong Kong
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Publikationsdatum:
23. April 2008 (online)

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Significance

The authors introduce the new P,S-ferrocenyl ligand 1 which, in combination with Pd(II), effectively promotes asymmetric allylic etherification of racemic allylic acetates. Using various alcohols under mild conditions, the products are obtained in good yields and excellent enantioselectivities. The pivotal finding reported here is the unprecedented observation of the effect of the electronic properties of alcohol substrates on the enantioselectivity of the reaction.