Asymmetric Synthesis of Borylalkanes via Copper-Catalyzed Enantioselective Hydroallylation.
An efficient synthetic method for preparing enantioenriched secondary borylalkanes has been achieved through a copper-catalyzed regio- and enantioselective hydroallylation of alkenyl boronates and boramides employing hydrosilanes and allylic phosphates. In the presence of a copper catalyst with a chiral Walphos ligand, a range of alkenylboron compounds with an aryl, heteroaryl, or alkyl substituent produced secondary homoallylic alkylboron compounds in good yields and with high enantioselectivities up to 99% ee. The utility of the resulting alkylboronates was demonstrated in an efficient synthesis of (S)-massoialactone.
Department of Chemistry and Institute of Basic Science, Sungkyunkwan University , Suwon 16419, Korea.
Jung Tae
JT
Han
Department of Chemistry and Institute of Basic Science, Sungkyunkwan University , Suwon 16419, Korea.
Won Jun
WJ
Jang
Department of Chemistry and Institute of Basic Science, Sungkyunkwan University , Suwon 16419, Korea.
Namhyeon
N
Kim
Department of Chemistry and Institute of Basic Science, Sungkyunkwan University , Suwon 16419, Korea.
Jaesook
J
Yun