SYN-ANTI ISOMERISM IN THE REACTIONS OF CIS-3,4-DISUBSTITUTED CYCLOBUTENES .6. CIS-DIHYDROXYLATION WITH OSO4

被引：16

作者：

BURDISSO, M

GANDOLFI, R

RASTELLI, A

机构：

[1] UNIV PAVIA,DIPARTMENTO CHIM ORGAN,V TARAMELLI 10,I-27100 PAVIA,ITALY

[2] UNIV MODENA,DIPARTMENTO CHIM,I-41100 MODENA,ITALY

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 23期

关键词：

D O I：

10.1016/S0040-4039(00)78812-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of 1 with OsO4 (carried out in acetone:water=2:1) takes place with moderate to high syn selectivity for X = Cl, OAc, OSO2Me, contrary to the predictions of Kishi's empirical rule but in accordance with the direction of the ground state out-of-plane bending of the olefinic hydrogens of cyclobutenes. Moreover, face selectivity observed is solvent dependent: a decrease in the syn:anti ratio was observed upon replacing methanol for water.

引用

页码：2659 / 2662

页数：4

共 28 条

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