Highly Stereoselective Cyclopropanation of Olefins Catalyzed by a Novel C₃-Symmetric Arsine

Abstract

A novel C ₃-symmetric arsine was employed in the one-pot cyclopropanation of olefins with carbonyl-stabilized arsonium ylides formed in situ from phenacyl bromide in the presence of NaHCO₃. This new arsine demonstrates good stereoselectivity and activity in the one-pot cyclopropanation of arylidenemalononitrile.

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GRAPHICAL ABSTRACT

Keywords:

• C ₃-symmetric arsine
• catalysis
• cyclopropanation
• stereoselectivity

ACKNOWLEDGMENTS

The authors thank the National Natural Science Foundation of China (No. 21261024) and the Science Foundation of Jiangxi Provincial Office of Education (GJJ10701, GJJ11706, GJJ12720 and GJJ12721) for financial support.

Notes

^a The reaction was carried out with triarsine 1 (0.15 equiv), phenacyl bromide (1.2 equiv), benzylidenemalononitrile (1.0 equiv), and base (3.0 equiv).

^b Reaction time and yield refer to triarsine 1.

^c Reaction time and yield refer to triphenylarsine.

^a The reaction was carried out with triarsine 1 (0.15 equiv), phenacyl bromide (1.2 equiv), arylidenemalononitrile (1.0 equiv), and NaHCO₃ (3.0 equiv) at 80 °C.

^b Yield of isolated product after silica-gel chromatography.