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Synfacts 2020; 16(12): 1470
DOI: 10.1055/s-0040-1719573
Organo- and Biocatalysis

Chiral Confinement Permits Enantiocontrolled Reactions To Proceed via Nonclassical Carbocations

Contributor(s):
Benjamin List
,
Yihang Li
Properzi R, Kaib PS. J, Leutzsch M, Pupo G, Mitra R, De CK, Song L, Schreiner PR, List B. * Max-Planck-Institut für Kohlenforschung, Mülheim an der Ruhr, Germany
Catalytic Enantiocontrol Over a Non-Classical Carbocation.

Nat. Chem. 2020;
DOI: 10.1038/s41557-020-00558-1
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Key words

imidodiphosphorimidate - asymmetric catalysis - nonclassical carbocations

Significance

Properzi et al. report a series of enantioselective reactions that are controlled by a confined chiral imidodiphosphorimidate catalyst and proceed via the renowned nonclassical 2-norbornyl cation intermediate. Spectroscopic and computational investigations were also conducted to support the proposed mechanisms.


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Comment

Nonclassical carbocations, such as the 2-norbornyl cation, were originally proposed by Saul Winstein in 1949, and their structural elucidation caused vivid discussions. In the highlighted paper, the authors present the first example of enantiocontrol over a nonclassical intermediate, namely the 2-norbornyl cation, contributing to its rich history. Moreover, several unprecedented activation modes for asymmetric organocatalysis are pioneered in this work.


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Publication History

Article published online:
17 November 2020

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