Hydroxy direction of zinc carbenoid addition to a remote olefin. Analysis and improvement of 2, 4-pentanediol tethered Furukawa cyclopropanation

…, M Yoshikawa, T Katagiri, R Miyashige, M Mizuguchi…

Index: Sugimura, Takashi; Futagawa, Tohru; Yoshikawa, Masato; Katagiri, Toshifumi; Miyashige, Ryoso; Mizuguchi, Miki; Nagano, Shinya; Sugimori, Seiji; Tai, Akira; Tei, Takahiro; Okuyama, Tadashi Tetrahedron, 2001 ,  vol. 57,  # 35  p. 7495 - 7499

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Citation Number: 11

Abstract

Zinc carbenoid addition to an olefin stereocontrolled by a chiral and remote intramolecular hydroxy group was studied in detail. Stereoselectivity as well as chemical yield of the Furukawa cyclopropanation was dramatically improved by modifications of the procedure of addition of the reagents. The structure of an active species to give the hydroxy-directed product is proposed.