Phosphine-Catalyzed Asymmetric Allylic Alkylation of Achiral MBH Carbonates with 3,3'-Bisindolines: Enantioselective Construction of Quaternary Stereogenic Centers

Chuan Xiang Alvin Tan; Guang-Jian Mei; Yixin Lu

doi:10.1021/acs.orglett.1c00201

Phosphine-Catalyzed Asymmetric Allylic Alkylation of Achiral MBH Carbonates with 3,3'-Bisindolines: Enantioselective Construction of Quaternary Stereogenic Centers

Org Lett. 2021 Mar 5;23(5):1787-1792. doi: 10.1021/acs.orglett.1c00201. Epub 2021 Feb 22.

Authors

Chuan Xiang Alvin Tan^{1

2}, Guang-Jian Mei^{1

3}, Yixin Lu^{1

2

4}

Affiliations

¹ Department of Chemistry, National University of Singapore, 3 Science Drive 3, 117543 Singapore.
² Graduate School for Integrative Sciences & Engineering (NGS), National University of Singapore, 28 Medical Drive, 117456 Singapore.
³ Green Catalysis Center and College of Chemistry, Zhengzhou University, Zhengzhou 450001, China.
⁴ Joint School of National University of Singapore and Tianjin University, International Campus of Tianjin University, Binhai New City, Fuzhou, Fujian 350207, China.

PMID: 33615793
DOI: 10.1021/acs.orglett.1c00201

Abstract

The asymmetric allylic alkylation (AAA) of achiral Morita-Baylis-Hillman (MBH) carbonates with 3,3'-bisindolines under the catalysis of amino-acid-derived bifunctional phosphines was accomplished. With the AAA approach introduced herein, challenging 3,3'-bisindolines bearing an all-carbon quaternary stereocenter (C3a) have been constructed in good yields with good to excellent enantioselectivties. In addition, the synthetic value of this protocol was demonstrated by the facile synthesis of the core skeleton of gliocladin C.

Publication types

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