Ni-Catalyzed Formation of Two Vicinal Enantioenriched C(sp3) Centers Stemming from Two Starting Materials

Mark Lautens; Xavier Abel-Snape

doi:10.1055/s-0042-1753404

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Synfacts 2023; 19(04): 0359
DOI: 10.1055/s-0042-1753404

Metals in Synthesis

Ni-Catalyzed Formation of Two Vicinal Enantioenriched C(sp³) Centers Stemming from Two Starting Materials

Contributor(s):

Mark Lautens

,

Xavier Abel-Snape

Bera S, Fan C, Hu X. * École Polytechnique Fédérale de Lausanne, Switzerland
Enantio- and Diastereoselective Construction of Vicinal C(sp ³) Centres via Nickel-Catalysed Hydroalkylation of Alkenes.

Nat. Cat. 2022;
5: 1180-1187
DOI: 10.1038/s41929-022-00894-0

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Abstract
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Key words

nickel catalysis - hydroalkylation - enantioselectivity - diastereoselectivity - radicals

Significance

The Hu group reports the first enantio- and diastereoselective Ni-catalyzed hydroalkylation of prochiral alkenes with a racemic mixture of a chiral alkyl halide. This report is the first example where control of a C(sp³)–C(sp³) bond formation occurs stereoselectively, as previous methodologies only lead to poor or modest diastereoselectivities.

Comment

The reaction generates products containing enantioenriched alkyl boronate and alkyl lactam moieties, which are both useful intermediates in organic synthesis. A ‘time study’ revealed that the racemic alkyl halides react through an enantioconvergent process instead of a kinetic resolution.

Publication History

Article published online:
17 March 2023

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

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