Yttrium-Catalyzed Intramolecular Hydroalkoxylation/Claisen Rearrangement Sequence: Efficient Synthesis of Medium-Sized Lactams

Bo Zhou; Long Li; Xin-Qi Zhu; Juan-Zhu Yan; Yi-Lin Guo; Long-Wu Ye

doi:10.1002/anie.201700596

Yttrium-Catalyzed Intramolecular Hydroalkoxylation/Claisen Rearrangement Sequence: Efficient Synthesis of Medium-Sized Lactams

Angew Chem Int Ed Engl. 2017 Mar 27;56(14):4015-4019. doi: 10.1002/anie.201700596. Epub 2017 Mar 7.

Authors

Bo Zhou¹, Long Li¹, Xin-Qi Zhu¹, Juan-Zhu Yan¹, Yi-Lin Guo¹, Long-Wu Ye^{1

2}

Affiliations

¹ Collaborative Innovation Center of Chemistry for Energy Material, State Key Laboratory of Physical Chemistry of Solid Surfaces, Key Laboratory for Chemical Biology of Fujian Province and College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, 361005, China.
² State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, 200032, China.

PMID: 28267264
DOI: 10.1002/anie.201700596

Abstract

An efficient yttrium-catalyzed intramolecular hydroalkoxylation/Claisen rearrangement sequence has been achieved, thus enabling facile access to a diverse array of valuable medium-sized lactams. Furthermore, a mechanistic rationale for this novel cascade reaction is well supported by a variety of control experiments.

Keywords: cyclization; heterocycles; homogeneous catalysis; rearrangements; yttrium.

Publication types

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