期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 25, 期 34, 页码 8013-8017出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201901406
关键词
diboronates; geminal diborylalkanes; homoallylboronates; lithium salts; S(N)2 mechanism
资金
- Spanish Ministerio de Economia y Competitividad (MINECO) [FEDER-CTQ2016-80328-P]
Vinyl epoxides and styrene oxide can react with diborylmethide lithium salts through an exclusive S(N)2 borylmethylation/ring opening in a regio- and diastereoselective way, depending on the nature of the substrate. The ring-opening protocol provides homoallylboronates that can be transformed into challenging diastereomeric bishomoallylic alicyclic 1,3-diols. Unprecedented 3-borylated 1,2-oxaborolan-2-ol products were prepared by borylmethylation/ring opening of 2-methyl-2-vinyloxirane followed by intramolecular cyclization.
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