One-pot synthesis of trans-β-lactams from ferrocenylketene generated by thermal Wolff rearrangement

ABSTRACT

A series of β-lactams containing the ferrocene moiety were synthesized through the Staudinger reaction between ferrocenylketene generated by the thermal Wolff rearrangement of the corresponding diazo ketone and various imines. The stereochemical outcome has been investigated and the trans-products were isolated as the main products, opposite to the reported results by Bonini and coworkers. The absolute configuration of (±)-trans-1,4-diphenyl-3-ferrocenylazetidin-2-one (3c) was determined by X-ray analysis. The stereoselectivity is discussed from the viewpoint of the reaction mechanism.

GRAPHICAL ABSTRACT

KEYWORDS:

• β-Lactams
• ferrocenyl-ketene
• stereoselectivity
• thermal Wolff rearrangement

Acknowledgments

This work was supported by the National Natural Science Foundation of China (No. 20702005), the Scientific Research Foundation for the Returned Overseas Chinese Scholars, State Education Ministry (No. LXKQ0802), and Fujian Provincial Natural Science Foundation of China (No. 2017J01577).

Additional information

Funding

This work was supported by the Scientific Research Foundation for the Returned Overseas Chinese Scholars, State Education Ministry [Grant Number No. LXKQ0802], Fujian Provincial Natural Science Foundation of China [Grant Number No. 2017J01577], and the National Natural Science Foundation of China [Grant Number No. 20702005].