Direct Catalytic Asymmetric Cyclopropylphosphonation Reactions of N

Letter Cite This: Org. Lett. XXXX, XXX, XXX−XXX

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Direct Catalytic Asymmetric Cyclopropylphosphonation Reactions of N,N-Dialkyl Groups of Aniline Derivatives by Ru(II)-Pheox Complex Chi Thi Loan Le, Seiya Ozaki, Soda Chanthamath, Kazutaka Shibatomi, and Seiji Iwasa* Department of Environmental and Life Sciences, Toyohashi University of Technology, 1-1 Hibarigaoka, Tempaku-cho, Toyohashi 441-8580, Japan

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S Supporting Information *

ABSTRACT: Novel catalysis involving phosphonomethylation of N-methylaniline and asymmetric cyclopropylphosphonation reactions of N,N-diethylaniline derivatives with diazomethylphosphonates are reported. Optically active cyclopropylphosphonate derivatives were directly synthesized from diazomethylphosphonates and N,N-diethylaniline derivatives catalyzed by a Ru(II)-Pheox complex in one step in good yields and high diastereoselectivities (up to trans/cis = > 99:1