Catalytic Asymmetric Mannich-Type Reaction of α-Haloacetonitriles.

Org Lett

Institute of Microbial Chemistry (BIKAKEN), 3-14-23 Kamiosaki, Shinagawa-ku, Tokyo 141-0021, Japan.

Published: September 2024

An asymmetric Mannich-type addition of aldimines and haloacetonitriles is reported here, yielding halogenated aminonitriles with excellent stereoselectivity, facilitated by a pincer Ni(II) complex as a catalyst. Haloacetonitriles are recognized as reactive electrophiles, and the possibility of their use as a pronucleophile has been almost neglected for many years. The resulting adduct can be readily converted into various valuable derivatives, including chiral aziridines, starting from chlorinated compounds.

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http://dx.doi.org/10.1021/acs.orglett.4c02505DOI Listing

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