Development and Analysis of a Pd(0)-Catalyzed Enantioselective 1,1-Diarylation of Acrylates Enabled by Chiral Anion Phase Transfer

Eiji Yamamoto; Margaret J. Hilton; Manuel Orlandi; Vaneet Saini; F. Dean Toste; Matthew S. Sigman

doi:10.1021/jacs.6b11367

Development and Analysis of a Pd(0)-Catalyzed Enantioselective 1,1-Diarylation of Acrylates Enabled by Chiral Anion Phase Transfer

Eiji Yamamoto, Margaret J. Hilton, Manuel Orlandi, Vaneet Saini, F. Dean Toste, Matthew S. Sigman

複合領域化学

研究成果: Contribution to journal › Article › 査読

68 被引用数 (Scopus)

抄録

Enantioselective 1,1-diarylation of terminal alkenes enabled by the combination of Pd catalysis with a chiral anion phase transfer (CAPT) strategy is reported herein. The reaction of substituted benzyl acrylates with aryldiazonium salts and arylboronic acids gave the corresponding 3,3-diarylpropanoates in moderate to good yields with high enantioselectivies (up to 98:2 er). Substituents on the benzyl acrylate and CAPT catalyst significantly affect the enantioselectivity, and multidimensional parametrization identified correlations suggesting structural origins for the high stereocontrol.

本文言語	英語
ページ（範囲）	15877-15880
ページ数	4
ジャーナル	Journal of the American Chemical Society
巻	138
号	49
DOI	https://doi.org/10.1021/jacs.6b11367
出版ステータス	出版済み - 12 14 2016

All Science Journal Classification (ASJC) codes

触媒
化学 (全般)
生化学
コロイド化学および表面化学

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Development and Analysis of a Pd(0)-Catalyzed Enantioselective 1,1-Diarylation of Acrylates Enabled by Chiral Anion Phase Transfer. / Yamamoto, Eiji; Hilton, Margaret J.; Orlandi, Manuel; Saini, Vaneet; Toste, F. Dean; Sigman, Matthew S.

In: Journal of the American Chemical Society, Vol. 138, No. 49, 14.12.2016, p. 15877-15880.

研究成果: Contribution to journal › Article › 査読

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abstract = "Enantioselective 1,1-diarylation of terminal alkenes enabled by the combination of Pd catalysis with a chiral anion phase transfer (CAPT) strategy is reported herein. The reaction of substituted benzyl acrylates with aryldiazonium salts and arylboronic acids gave the corresponding 3,3-diarylpropanoates in moderate to good yields with high enantioselectivies (up to 98:2 er). Substituents on the benzyl acrylate and CAPT catalyst significantly affect the enantioselectivity, and multidimensional parametrization identified correlations suggesting structural origins for the high stereocontrol.",

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