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 - Zhou, Wang
AU - Shiratori, Yota
AU - Stewart, Scott G.
AU - Murakami, Masahiro
N1 - Funding Information:
This work was supported by Grants-in-Aid for Scientific Research (S) (JP15H05756) and (C) (JP16K05694) from MEXT and the ACT-C Program (JPMJCR12Z9) from the JST. W.Z. acknowledges a JSPS postdoctoral fellowship for foreign researchers. S.G.S. acknowledges an invitation fellowship for research from The Kyoto University Foundation.
Publisher Copyright:
© 2017 American Chemical Society.
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.
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U2 - 10.1021/jacs.7b06408
DO - 10.1021/jacs.7b06408
M3 - Article
C2 - 28708391
AN - SCOPUS:85027154169
SN - 0002-7863
VL - 139
SP - 10903
EP - 10908
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
IS - 31
ER -