Display options
Cite
Pearson AJ, Gontcharov AV. Asymmetric Conversion of Arenechromium Complexes to Functionalized Cyclohexenones: Progress toward Defining an Optimum Chiral Auxiliary. J Org Chem. 1998;63(1):152-162doi: 10.1021/jo971676o.
Pearson, A. J., & Gontcharov, A. V. (1998). Asymmetric Conversion of Arenechromium Complexes to Functionalized Cyclohexenones: Progress toward Defining an Optimum Chiral Auxiliary. The Journal of organic chemistry, 63(1), 152-162. https://doi.org/10.1021/jo971676o
Pearson, Anthony J., and Gontcharov, Alexander V.. "Asymmetric Conversion of Arenechromium Complexes to Functionalized Cyclohexenones: Progress toward Defining an Optimum Chiral Auxiliary." The Journal of organic chemistry vol. 63,1 (1998): 152-162. doi: https://doi.org/10.1021/jo971676o
Pearson AJ, Gontcharov AV. Asymmetric Conversion of Arenechromium Complexes to Functionalized Cyclohexenones: Progress toward Defining an Optimum Chiral Auxiliary. J Org Chem. 1998 Jan 09;63(1):152-162. doi: 10.1021/jo971676o. PMID: 11674056.
Copy Download .nbib Format: NLM
Share it on

J Org Chem. 1998 Jan 09;63(1):152-162. doi: 10.1021/jo971676o.

Asymmetric Conversion of Arenechromium Complexes to Functionalized Cyclohexenones: Progress toward Defining an Optimum Chiral Auxiliary.

The Journal of organic chemistry

Anthony J. Pearson, Alexander V. Gontcharov

Affiliations

  1. Department of Chemistry, Case Western Reserve University, Cleveland, Ohio 44106.

PMID: 11674056 DOI: 10.1021/jo971676o

Abstract

An investigation into the asymmetric synthesis of 5-substituted cyclohexenones via nucleophile addition to (alkoxyarene)chromium tricarbonyl complexes is described. Diastereoselectivity during the nucleophile addition step was achieved using alkoxy substituents derived from terpenoid substrates as chiral auxiliaries. Selectivities as high as 24:1 were obtained when 2-phenylisoborneol was used as the chiral auxiliary and as high as 17:1 using 3,3-(ethylenedioxy)isoborneol. The absolute stereochemistry of the major products was assigned by Mosher's method, after their conversion to the corresponding cyclohexenol. A study of the temperature dependence of the nucleophile addition to alkoxytoluene complexes revealed a thermodynamic preference for addition ortho to the ether substituent.

Publication Types