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Palladium-Catalyzed Asymmetric Addition of Pronucleophiles to Allenes

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Department of Chemistry, Stanford University, Stanford, California 94305-5080
Cite this: J. Am. Chem. Soc. 2003, 125, 15, 4438–4439
Publication Date (Web):March 25, 2003
https://doi.org/10.1021/ja029190z
Copyright © 2003 American Chemical Society
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    Abstract

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    Simple additions are the most atom economic way to effect alkylations. The ability to effect the hydrocarbonation of allenes asymmetrically then becomes a highly efficient alkylation protocol. The first example of such a protocol involves the ability of a palladium(0) catalyst derived from palladium trifluoroacetate dimer and the bis-2-diphenylphosphinobenzamide of trans-1,2-diamininocyclohexane to catalyze additions to benzyloxyalkene. Various substituted Meldrum's acids including hydroxy Meldrum's acid react well in the presence of 1 mol % trifluoroacetic acid to give one regioisomer with ee's ranging from 82 to 99%. Switching to azlactones to access unusual quarternary amino acids requires somewhat more basic conditions. Thus, use of 2 mol % potassium α-butoxide and 20 mol % hippuric acid leads to a smooth reaction to produce a simple regiosomer. This nucleophile raises the question of facial selectivity with respect to both the nucleophile and the electrophile. Excellent diastereoselectivity (dr 13−20:1) and enantioselectivity (85−94% ee) are obtained. Thus, a new approach for asymmetric allylic alkylations of carbon pronucleophiles by simple additions provides a very efficient, more atom economic strategy for asymmetric C−C bond formation.

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    Spectroscopic and analytical data for 5a−f and 8a−e and representative procedures for the synthesis of 5a and 8a (PDF). This material is available free of charge via the Internet at http://pubs.acs.org.

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