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Asymmetric synthesis of chiral 9,10-dihydrophenanthrenes using Pd-catalyzed asymmetric intramolecular Friedel-Crafts allylic alkylation of phenols.
Org Lett. 2012 May 04; 14(9):2350-3.OL

Abstract

We developed a novel asymmetric synthetic method for multisubstituted 9,10-dihydrophenanthrenes based on the Pd-catalyzed asymmetric intramolecular Friedel-Crafts allylic alkylation of phenols, which produces 10-vinyl or 10-isopropenyl chiral 9,10-dihydrophenanthrene derivatives in high yield with up to 94% ee.

Authors+Show Affiliations

Graduate School of Pharmaceutical Sciences, Chiba University, 1-8-1 Inohana, Chuo-ku, Chiba 260-8675, Japan.No affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

22509956

Citation

Suzuki, Yuta, et al. "Asymmetric Synthesis of Chiral 9,10-dihydrophenanthrenes Using Pd-catalyzed Asymmetric Intramolecular Friedel-Crafts Allylic Alkylation of Phenols." Organic Letters, vol. 14, no. 9, 2012, pp. 2350-3.
Suzuki Y, Nemoto T, Kakugawa K, et al. Asymmetric synthesis of chiral 9,10-dihydrophenanthrenes using Pd-catalyzed asymmetric intramolecular Friedel-Crafts allylic alkylation of phenols. Org Lett. 2012;14(9):2350-3.
Suzuki, Y., Nemoto, T., Kakugawa, K., Hamajima, A., & Hamada, Y. (2012). Asymmetric synthesis of chiral 9,10-dihydrophenanthrenes using Pd-catalyzed asymmetric intramolecular Friedel-Crafts allylic alkylation of phenols. Organic Letters, 14(9), 2350-3. https://doi.org/10.1021/ol300770w
Suzuki Y, et al. Asymmetric Synthesis of Chiral 9,10-dihydrophenanthrenes Using Pd-catalyzed Asymmetric Intramolecular Friedel-Crafts Allylic Alkylation of Phenols. Org Lett. 2012 May 4;14(9):2350-3. PubMed PMID: 22509956.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Asymmetric synthesis of chiral 9,10-dihydrophenanthrenes using Pd-catalyzed asymmetric intramolecular Friedel-Crafts allylic alkylation of phenols. AU - Suzuki,Yuta, AU - Nemoto,Tetsuhiro, AU - Kakugawa,Kazumi, AU - Hamajima,Akinari, AU - Hamada,Yasumasa, Y1 - 2012/04/17/ PY - 2012/4/19/entrez PY - 2012/4/19/pubmed PY - 2012/7/26/medline SP - 2350 EP - 3 JF - Organic letters JO - Org Lett VL - 14 IS - 9 N2 - We developed a novel asymmetric synthetic method for multisubstituted 9,10-dihydrophenanthrenes based on the Pd-catalyzed asymmetric intramolecular Friedel-Crafts allylic alkylation of phenols, which produces 10-vinyl or 10-isopropenyl chiral 9,10-dihydrophenanthrene derivatives in high yield with up to 94% ee. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/22509956/Asymmetric_synthesis_of_chiral_910_dihydrophenanthrenes_using_Pd_catalyzed_asymmetric_intramolecular_Friedel_Crafts_allylic_alkylation_of_phenols_ L2 - https://doi.org/10.1021/ol300770w DB - PRIME DP - Unbound Medicine ER -