Chiral recyclable fluorous disulfonamide ligand for catalytic enantioselective cyclopropanation of allylic alcohols. Issue 45 (11th November 2015)

• Record Type: Journal Article
• Authors: Kawashima, Yuya; Ezawa, Tetsuya; Yamamura, Mai; Harada, Taisuke; Noguchi, Takuya; Miura, Tsuyoshi; Imai, Nobuyuki
• Is Part Of: Tetrahedron. Volume 71:Issue 45(2015)
• Page Start: 8585
• Page End: 8592
• Publication Date: 2015-11-11
• Subjects: Enantioselectivity -- Simmons–Smith cyclopropanation -- Fluorous disulfonamide -- Chiral ligand -- Recycle; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2015.09.024
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: Allylic alcohols reacted with Et2 Zn and CH2 I2 in the presence of a catalytic amount of fluorous disulfonamide 3a to afford the corresponding cyclopropylmethanols in 69%-quantitative yields with 49–85% ee. Recovery of the fluorous ligand 3a was readily performed from the reaction mixture by the fluorous solid-phase extraction (FSPE), and the recovered 3a could be reused without a significant loss of the catalytic activity and enantioselectivity. Graphical abstract: