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γ-Selective Directed Catalytic Asymmetric Hydroboration of 1,1-disubstituted Alkenes

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Specialty Chemistry
Date 2012 Nov 13
PMID 23145431
Citations 14
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Abstract

Directed catalytic asymmetric hydroborations of 1,1-disubstituted alkenes afford γ-dioxaborato amides and esters in high enantiomeric purity (90-95% ee).

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References
1.
Scott H, Aggarwal V . Highly enantioselective synthesis of tertiary boronic esters and their stereospecific conversion to other functional groups and quaternary stereocentres. Chemistry. 2011; 17(47):13124-32. DOI: 10.1002/chem.201102581. View

2.
Mazet C, Gerard D . Highly regio- and enantioselective catalytic asymmetric hydroboration of α-substituted styrenyl derivatives. Chem Commun (Camb). 2010; 47(1):298-300. DOI: 10.1039/c0cc01547d. View

3.
Awano T, Ohmura T, Suginome M . Inversion or retention? Effects of acidic additives on the stereochemical course in enantiospecific Suzuki-Miyaura coupling of α-(acetylamino)benzylboronic esters. J Am Chem Soc. 2011; 133(51):20738-41. DOI: 10.1021/ja210025q. View

4.
Schuster C, Li B, Morken J . Modular monodentate oxaphospholane ligands: utility in highly efficient and enantioselective 1,4-diboration of 1,3-dienes. Angew Chem Int Ed Engl. 2011; 50(34):7906-9. PMC: 3365687. DOI: 10.1002/anie.201102404. View

5.
Smith S, Takacs J . Remarkable levels of enantioswitching in catalytic asymmetric hydroboration. Org Lett. 2010; 12(20):4612-5. PMC: 3033434. DOI: 10.1021/ol101932q. View