A novel synthetic route to isolable pentacoordinate 1, 2-oxaphosphetanes and mechanism of their thermolysis, the second step of the Wittig reaction

T Kawashima, K Kato, R Okazaki

Index: Kawashima, Takayuki; Kato, Katsuhiro; Okazaki, Renji Journal of the American Chemical Society, 1992 , vol. 114, # 10 p. 4008 - 4010

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Citation Number: 56

Abstract

14: R,R - TPOS; 5: R I R - H; 6 R I TBDMS. I? - H; 7 R I TBOMS, R' I C(S)OPh I: B I adenin-4yl: b B - uracikl-yl: c: E - J-Nbemoybracikl-yl: Bll: R - TBOMS. ... 2'-deoxynucleoside-2'-spiropyrazoline derivatives 2a (88%) and 3a (4%) (Scheme I). The stereochemistry of 2a(2'R) and 3a(2'S) was assigned from 2D ROESY NMR experiments with each compound. Thus, diazomethane cycloaddition occurred prefer- entially from the less hindered a-face to give 2a as the major isomer, ...