Open AccessCopper-Catalyzed, Stereoselective Cross-Coupling of Cyclic Allyl Boronic Acids with α-Diazoketones
Author(s) -
Dong Wang,
Kálmán J. Szabó
Publication year - 2017
Publication title -
organic letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/acs.orglett.7b00433
Subject(s) - transmetalation , chemistry , stereoselectivity , substrate (aquarium) , catalysis , copper , carbene , coupling (piping) , combinatorial chemistry , stereochemistry , organic chemistry , mechanical engineering , oceanography , engineering , geology
In this study, we present the synthesis of new, stereodefined allylboronic acids employed to investigate the stereochemistry of the Cu-catalyzed cross-coupling of allylboronic acids with α-diazoketones. According to our results, this reaction proceeds with retention of the relative configuration of the allylboronic acid substrate. We suggest that the stereoinduction step involves a syn S E 2'-type transmetalation of the allylboronic acid substrate with a Cu-carbene species.