Enantioselective assembly of tertiary stereocenters via multicomponent chemoselective cross-coupling of geminal chloro(iodo)alkanes

X. Jiang, K. Kulbitski, G. Nisnevich, M. Gandelman

Research output: Contribution to journalArticlepeer-review

9 Scopus citations


Tertiary stereocenters represent a ubiquitous and highly important motif in many pharmaceutically active compounds and natural products. Development of efficient and straightforward approaches to their enantioselective construction from readily available simple substrates is an important yet challenging goal for synthetic chemistry. Herein we describe an efficient, versatile and facile method for the highly enantioselective construction of tertiary stereocenters via unprecedented consecutive one-pot Suzuki reactions of non-activated racemic 1-chloro-1-iodoalkanes with alkylboranes. It represents the first cross-coupling approach which employs simple and readily available primary alkyl substrates for the direct multicomponent assembly of enantioenriched tertiary stereocenters. A simple and effective preparation of 1-chloro-1-iodoalkanes from ubiquitous α-chloroalkanoic acids is also described. Collectively, the developed methods open a door to efficient catalytic enantioselective synthesis of alkanes bearing tertiary stereocenters from carboxylic acids just in few steps.

Original languageEnglish
Pages (from-to)2762-2767
Number of pages6
JournalChemical Science
Issue number4
StatePublished - 21 Apr 2016
Externally publishedYes

Bibliographical note

Publisher Copyright:
© The Royal Society of Chemistry 2016.


We acknowledge the financial support from German-Israeli Project Cooperation (DIP) and Israel Science Foundation personal grant (1890/15).

FundersFunder number
German-Israeli Project Cooperation
Israel Science Foundation1890/15


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