The authors acknowledge partial funding of this work by the Donors of the Petroleum Research Fund, administered by the American Chemical Society (PRF #37868-G1) and Research Corporation (Research Innovation Award to J.S.J.).
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Communication
Kinetic Control in Direct α-Silyloxy Ketone Synthesis: A New Regiospecific Catalyzed Cross Silyl Benzoin Reaction†
Article first published online: 5 JUN 2003
DOI: 10.1002/anie.200250554
Copyright © 2003 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Linghu, X. and Johnson, J. S. (2003), Kinetic Control in Direct α-Silyloxy Ketone Synthesis: A New Regiospecific Catalyzed Cross Silyl Benzoin Reaction. Angewandte Chemie International Edition, 42: 2534–2536. doi: 10.1002/anie.200250554
- †
Publication History
- Issue published online: 5 JUN 2003
- Article first published online: 5 JUN 2003
- Manuscript Received: 14 NOV 2002
Keywords:
- benzoin condensation;
- ketones;
- phase-transfer catalysis;
- rearrangements;
- umpolung
Graphical Abstract
Side-stepping thermodynamics. In contrast to the traditional benzoin reaction, which can yield a mixture of homo and mixed adducts, only one regioisomer was obtained from the new cyanide-catalyzed silyl benzoin reaction between acylsilanes and aldehydes (see scheme).