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Synfacts 2016; 12(12): 1301
DOI: 10.1055/s-0036-1589631
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart · New York

Highly Enantioselective Addition of Allyltrimethylsilane to Aldehydes

Contributor(s):
Benjamin List
,
Grigory A. Shevchenko
Kaib PS. J, Schreyer L, Lee S, Properzi R, List B * Max-Planck-Institut für Kohlenforschung, Mülheim an der Ruhr, Germany
Extremely Active Organocatalysts Enable a Highly Enantioselective Addition of Allyltrimethylsilane to Aldehydes.

Angew. Chem. Int. Ed. 2016;
55: 13200-13203
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Further Information

Publication History

Publication Date:
17 November 2016 (online)

 
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Key words

silylium Lewis acids - Hosomi–Sakurai reaction - aldehydes - allyltrimethylsilane - imidodiphosphorimidates - asymmetric catalysis

Significance

List and co-workers report the first general, highly enantioselective, organocatalytic addition of allyltrimethylsilane to aldehydes (the Hosomi–Sakurai reaction). This transformation is enabled by newly developed highly confined imido­diphosphorimidates IDPi. Various aromatic and aliphatic aldehydes are tolerated under the reaction conditions, affording the desired products in good to excellent yields and enantioselectivities (er ≤ 98:2).


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Comment

The IDPi motif, which can be accessed by a single-flask synthesis from 3,3′-disubstituted BINOL derivatives, is a combination of the recently developed highly confined imidodiphosphates (Nature 2012, 483, 315) and highly acidic BINOL-derived phosphoramidimidates (Synlett 2016, 27, 156).


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