Enantioselective C--C bond formation to sulfonylimines through use of the 2-pyridinesulfonyl group as a novel stereocontroller.
Enantioselective C--C bond formation to 2-pyridinesulfonylimines afforded products with good enantioselectivity. Dynamic induction of chirality on the sulfur by coordination of a chiral Lewis acid to the pyridine nitrogen and one of the prochiral sulfonyl oxygens induces enantioselectivity. Since the 2-pyridinesulfonyl group can easily be removed after the reaction, it acts not only as an activating group but also as an efficient stereocontroller.
Nakamura
Shuichi
S
Department of Applied Chemistry, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555, Japan. snakamur@nitech.ac.jp
Nakashima
Hiroki
H
Sugimoto
Hideki
H
Sano
Hideaki
H
Hattori
Masataka
M
Shibata
Norio
N
Toru
Takeshi
T
D002244:Carbon / Q000737:chemistry*; D007097:Imines / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011725:Pyridines / Q000737:chemistry*; D013237:Stereoisomerism; D013450:Sulfones / Q000138:chemical synthesis* / Q000737:chemistry*
D007097:Imines; D011725:Pyridines; D013450:Sulfones; D002244:Carbon