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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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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.


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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.


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Publication History

Article published online:
17 March 2023

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