TY - JOUR
T1 - Diastereo- and Enantioselective Synthesis of (E)-δ-Boryl-Substituted anti-Homoallylic Alcohols in Two Steps from Terminal Alkynes
AU - Miura, Tomoya
AU - Oku, Naoki
AU - Murakami, Masahiro
N1 - Funding Information:
This work was supported by MEXT [Grants‐in‐Aids for Scientific Research (S) (15H05756)] and ISHIZUE 2019 of Kyoto University Research Development Program. We thank Mr. J. Nakahashi (Kyoto Univ.) for his contribution at a preliminary stage.
Publisher Copyright:
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
PY - 2019/10/7
Y1 - 2019/10/7
N2 - We report the highly diastereo- and enantioselective preparation of (E)-δ-boryl-substituted anti-homoallylic alcohols in two steps from terminal alkynes. This method consists of a cobalt(II)-catalyzed 1,1-diboration reaction of terminal alkynes with B2pin2 and a palladium(I)-mediated asymmetric allylation reaction of the resulting 1,1-di(boryl)alk-1-enes with aldehydes in the presence of a chiral phosphoric acid. Propyne, which is produced as the byproduct during petroleum refining, could be used as the starting material to construct homoallylic alcohols that are otherwise difficult to synthesize with high stereocontrol.
AB - We report the highly diastereo- and enantioselective preparation of (E)-δ-boryl-substituted anti-homoallylic alcohols in two steps from terminal alkynes. This method consists of a cobalt(II)-catalyzed 1,1-diboration reaction of terminal alkynes with B2pin2 and a palladium(I)-mediated asymmetric allylation reaction of the resulting 1,1-di(boryl)alk-1-enes with aldehydes in the presence of a chiral phosphoric acid. Propyne, which is produced as the byproduct during petroleum refining, could be used as the starting material to construct homoallylic alcohols that are otherwise difficult to synthesize with high stereocontrol.
KW - allylation
KW - asymmetric catalysis
KW - double-bond transposition
KW - homoallylic compounds
KW - palladium
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U2 - 10.1002/anie.201908299
DO - 10.1002/anie.201908299
M3 - Article
C2 - 31392816
AN - SCOPUS:85071646534
VL - 58
SP - 14620
EP - 14624
JO - Angewandte Chemie - International Edition
JF - Angewandte Chemie - International Edition
SN - 1433-7851
IS - 41
ER -