TY - JOUR
T1 - Enantioselective Synthesis of anti-1,2-Oxaborinan-3-enes from Aldehydes and 1,1-Di(boryl)alk-3-enes Using Ruthenium and Chiral Phosphoric Acid Catalysts
AU - Miura, Tomoya
AU - Nakahashi, Junki
AU - Zhoi, Wang
AU - Shiratori, Yota
AU - Stewart, Scott
AU - Murakami, Masahiro
PY - 2017/8/9
Y1 - 2017/8/9
N2 - A cationic ruthenium(II) complex catalyzes double-bond transposition of 1,1-di(boryl)alk-3-enes to generate in situ 1,1-di(boryl)alk-2-enes, which then undergo chiral phosphoric acid catalyzed allylation of aldehydes producing homoallylic alcohols with a (Z)-vinylboronate moiety. 1,2-Anti stereochemistry is installed in an enantioselective manner. The (Z)-geometry forged in the products allows their isolation in a form of 1,2-oxaborinan-3-enes, upon which further synthetic transformations are operated.
AB - A cationic ruthenium(II) complex catalyzes double-bond transposition of 1,1-di(boryl)alk-3-enes to generate in situ 1,1-di(boryl)alk-2-enes, which then undergo chiral phosphoric acid catalyzed allylation of aldehydes producing homoallylic alcohols with a (Z)-vinylboronate moiety. 1,2-Anti stereochemistry is installed in an enantioselective manner. The (Z)-geometry forged in the products allows their isolation in a form of 1,2-oxaborinan-3-enes, upon which further synthetic transformations are operated.
U2 - 10.1021/jacs.7b06408
DO - 10.1021/jacs.7b06408
M3 - Article
C2 - 28708391
SN - 0002-7863
VL - 139
SP - 10903
EP - 10908
JO - Journal of the Amercian Chemical Society
JF - Journal of the Amercian Chemical Society
IS - 31
ER -