期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 22, 期 14, 页码 4723-4726出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201600392
关键词
1; 2-diboron; configuration; crystalline sponge method; diboron inclusion; organocatalysis
资金
- Spanish Ministerio de Economia y Competitividad (MINECO) [CTQ2013-43395P, CTQ2013-50219-EXP]
- JST-ACCEL
The stereochemical outcome of the recently developed metal-free 1,2-diboration of aliphatic alkenes has, until now, only been elucidated by indirect means (e.g. derivatization). This is because classical conformational analysis of the resulting 1,2-diboranes is not viable; in the (HNMR)-H-1 spectrum the relevant H-1 resonances are broadened by B-11, and the occurrence of the products as oily compounds precludes X-ray crystallographic analysis. Herein, the crystalline sponge method is used to display the crystal structures of the diboronic esters formed from internal E and Z olefins, evidencing the stereospecific syn addition mechanism of the reaction, which is fully consistent with the prediction from DFT calculations.
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