Control of Vicinal Stereocenters through Nickel-Catalyzed Alkyl–Alkyl Cross-Coupling

Xin Mu, Yu Shibata, Yusuke Makida, Gregory C. Fu

Research output: Contribution to journalArticle

18 Citations (Scopus)

Abstract

Vicinal stereocenters are found in many natural and unnatural compounds. Although metal-catalyzed cross-coupling reactions of unactivated alkyl electrophiles are emerging as a powerful tool in organic synthesis, there have been virtually no reports of processes that generate, much less control, vicinal stereocenters. In this investigation, we establish that a chiral nickel catalyst can mediate doubly stereoconvergent alkyl–alkyl cross-coupling, specifically, reactions of a racemic pyrrolidine-derived nucleophile with cyclic alkyl halides (as mixtures of stereoisomers) to produce vicinal stereocenters with very good stereoselectivity.

Original languageEnglish
Pages (from-to)5821-5824
Number of pages4
JournalAngewandte Chemie - International Edition
Volume56
Issue number21
DOIs
Publication statusPublished - Jan 1 2017

Fingerprint

Stereoselectivity
Nucleophiles
Stereoisomerism
Nickel
Metals
Catalysts
pyrrolidine

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

Cite this

Control of Vicinal Stereocenters through Nickel-Catalyzed Alkyl–Alkyl Cross-Coupling. / Mu, Xin; Shibata, Yu; Makida, Yusuke; Fu, Gregory C.

In: Angewandte Chemie - International Edition, Vol. 56, No. 21, 01.01.2017, p. 5821-5824.

Research output: Contribution to journalArticle

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