Scandium Triflate–Promoted Addition of Organozinc Reagents to Benzaldiminetricarbonylchromium Derivatives

Abstract

The reaction of benzaldiminetricarbonylchromium derivatives with organozinc reagents in the presence of scandium triflate afforded a single diastereomer of the corresponding amine complex exclusively. Even in the case of benzaldiminetricarbonylchromium having an m‐substituent of the aromatic ring, one diastereomer was obtained using the o‐TMS‐protected chromium complex. The TMS group and the chromium moiety were easily removed and the benzyl group was deprotected using HOOH and Pd to afford the corresponding amine.

Keywords:

• imines
• organozinc reagents
• stereocontrol

Acknowledgment

We thank Shinji Ohta and Mihoko Yanai, the Instrument Center for Chemical Analysis, Hiroshima University, for help with the measurement of HRMS.