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Synfacts 2006(11): 1181-1181  
DOI: 10.1055/s-2006-949404
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

Polymer-Support Synthesis of Chiral Tertiary Alcohols

Contributor(s): Yasuhiro Uozumi, Hiroe Takenaka
V. J. Forrat, D. J. Ramón*, M. Yus*
Universidad de Alicante, Spain
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Publication History

Publication Date:
24 October 2006 (online)

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Significance

Polymer-supported trans-1-phenylsulfonylamino-2-(isoborneolsulfonylamino)cyclohexane ligands 1a-d were prepared and used in the catalytic enantioselective addition of organo­zinc reagents to ketones. The addition reactions of diethylzinc to acetophenone with ligands 1 in the presence of Ti(Oi-Pr)4 at 25 °C in toluene gave the tertiary alcohol 2 with high enantioselectivity, although the yields were low (eq. 1). Arylation of several kinds of ketones using the soluble polymer 1d (non-cross-linked) with Et2Zn/BPh3 in the presence of Ti(Oi-Pr)4 gave the corresponding alcohols in 54-99% yield with 38-90% ee (eq. 2).