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Enantioselective Cyanosilylation of Ketones Catalyzed by a Chiral Oxazaborolidinium Ion.

✍ Scribed by Do Hyun Ryu; E. J. Corey

Publisher
John Wiley and Sons
Year
2005
Weight
25 KB
Volume
36
Category
Article
ISSN
0931-7597

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✦ Synopsis

2005 Cyanation O 0273 Enantioselective Cyanosilylation of Ketones Catalyzed by a Chiral Oxazaborolidinium Ion. -Chiral oxazaborolidinium triflate (Ib) represents an efficient catalyst for the cyanosilylation of methyl ketones (II) and (V). The reaction proceeds with a reactive Ph2MePOTms(N=C:) intermediate generated from TmsCN and Me-POPh2. Excellent stereoselectivity is achieved for acetophenones containing electron-withdrawing para-substituents (IIc) and (IId), while inferior results and opposite stereoinduction is obtained in the presence of electron-donating aryl substituents [cf. (V)]. The reaction mechanism is discussed in detail. -(RYU, D. H.; COREY*, E.

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Enantioselective Cyanosilylation of Keto
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## Abstract An efficient and optically active, bifunctional tetraaza ligand (2__S__)‐__N__‐{(1__R__,2__R__)‐2‐[(__S__)‐pyrrolidine‐2‐carboxamido]‐1,2‐diphenylethyl}pyrrolidine‐2‐carboxamide has been developed for the addition of trimethylsilyl cyanide (TMSCN) to ketones. The bifunctional catalyst s