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Enantioselective C--C bond formation to sulfonylimines through use of the 2-pyridinesulfonyl group as a novel stereocontroller
Authors:Nakamura Shuichi  Nakashima Hiroki  Sugimoto Hideki  Sano Hideaki  Hattori Masataka  Shibata Norio  Toru Takeshi
Affiliation:Department of Applied Chemistry, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555, Japan. snakamur@nitech.ac.jp
Abstract:
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.
Keywords:asymmetric synthesis  Grignard reactions  Mannich‐type reactions  stereocontroller  Strecker‐type reaction
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