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2005
Ketones
Q 0350
25- 076
Mechanism and Scope of the Cyanide-Catalyzed Cross Silyl Benzoin Reaction.
— The reaction of acylsilanes with aldehydes is investigated in the presence of either
catalytic amounts of KCN/18-crown-6 or by use of La(CN)3 as improved second-generation catalyst. Unsymmetrical aryl-, heteroaryl-, and alkyl-substituted benzoin adducts are obtained in moderate to excellent yields with complete regiocontrol. A study
concerning the influence of water on the KCN-catalyzed reaction reveals more practical reaction conditions using unpurified Et2O under ambient conditions. Bu4NCN is
tested as an alternative catalyst for the reaction of acylsilane (VI) and provides the corresponding product in good yield within 30 minutes. A sequential silyl benzoin addition/cyanation/O-acylation reaction that result in the formation of silyl cyanohydrin
carbonates (XVIII) and (XX) is also achieved. — (LINGHU, X.; BAUSCH, C. C.;
JOHNSON*, J. S.; J. Am. Chem. Soc. 127 (2005) 6, 1833-1840; Dep. Chem., Univ.
N. C., Chapel Hill, NC 27599, USA; Eng.) — Klein
2005
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