Palladium-Catalyzed Asymmetric Construction of Vicinal Tertiary and All-Carbon Quaternary Stereocenters by Allylation of β-Ketocarbonyls with Morita-Baylis-Hillman Adducts

Jiawang Liu; Zhaobin Han; Xiaoming Wang; Fanye Meng; Zheng Wang; Kuiling Ding

doi:10.1002/anie.201701455

Palladium-Catalyzed Asymmetric Construction of Vicinal Tertiary and All-Carbon Quaternary Stereocenters by Allylation of β-Ketocarbonyls with Morita-Baylis-Hillman Adducts

Angew Chem Int Ed Engl. 2017 Apr 24;56(18):5050-5054. doi: 10.1002/anie.201701455. Epub 2017 Apr 5.

Authors

Jiawang Liu^{1

2}, Zhaobin Han¹, Xiaoming Wang¹, Fanye Meng^{1

2}, Zheng Wang¹, Kuiling Ding^{1

2

3}

Affiliations

¹ State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, China.
² University of Chinese Academy of Sciences, Beijing, 100049, China.
³ Collaborative Innovation Center of Chemical Science and Engineering, Tianjin, 300071, China.

PMID: 28378466
DOI: 10.1002/anie.201701455

Abstract

Palladium-catalyzed regio-, diastereo-, and enantioselective allylic alkylation of β-ketocarbonyls with Morita-Baylis-Hillman adducts has been developed using a spiroketal-based diphosphine (SKP) as the ligand, thus affording a range of densely functionalized products bearing vicinal tertiary and all-carbon quaternary stereodyad in high selectivities. The utility of the protocol was demonstrated by the facile synthesis of some complex molecules by simple product transformations.

Keywords: P ligands; allylic compounds; asymmetric catalysis; palladium; spiro compounds.

Publication types

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