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Trost BM, Ryan MC. A Ruthenium/Phosphoramidite-Catalyzed Asymmetric Interrupted Metallo-ene Reaction. J Am Chem Soc. 2016;138(9):2981-4doi: 10.1021/jacs.6b00983.
Trost, B. M., & Ryan, M. C. (2016). A Ruthenium/Phosphoramidite-Catalyzed Asymmetric Interrupted Metallo-ene Reaction. Journal of the American Chemical Society, 138(9), 2981-4. https://doi.org/10.1021/jacs.6b00983
Trost, Barry M, and Ryan, Michael C. "A Ruthenium/Phosphoramidite-Catalyzed Asymmetric Interrupted Metallo-ene Reaction." Journal of the American Chemical Society vol. 138,9 (2016): 2981-4. doi: https://doi.org/10.1021/jacs.6b00983
Trost BM, Ryan MC. A Ruthenium/Phosphoramidite-Catalyzed Asymmetric Interrupted Metallo-ene Reaction. J Am Chem Soc. 2016 Mar 09;138(9):2981-4. doi: 10.1021/jacs.6b00983. Epub 2016 Mar 01. PMID: 26899551.
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J Am Chem Soc. 2016 Mar 09;138(9):2981-4. doi: 10.1021/jacs.6b00983. Epub 2016 Mar 01.

A Ruthenium/Phosphoramidite-Catalyzed Asymmetric Interrupted Metallo-ene Reaction.

Journal of the American Chemical Society

Barry M Trost, Michael C Ryan

Affiliations

  1. Department of Chemistry, Stanford University , Stanford, California 94305-5580, United States.

PMID: 26899551 DOI: 10.1021/jacs.6b00983

Abstract

Allylic chlorides prepared from commercially available trans-1,4-dichloro-2-butene were converted to trans-disubstituted 5- and 6-membered ring systems with perfect diastereoselectivity and high enantioselectivity under chiral ruthenium catalysis. These products contain stereodefined secondary and tertiary alcohols that originate from the trapping of an alkylruthenium intermediate with adventitious water. Key to the success of this transformation was the development of a new BINOL-based phosphoramidite ligand containing bulky substitution at its 3- and 3'-positions. As a demonstration of product utility, diastereoselective Friedel-Crafts reactions were performed on the chiral benzylic alcohols in high yield and stereoselectivity.

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