3-Boronoacrolein as an Exceptional Heterodiene in the Highly Enantio- and Diastereoselective Cr(III)-Catalyzed Three-Component [4+2]/Allylboration
- 15 July 2003
- journal article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 125 (31), 9308-9309
- https://doi.org/10.1021/ja036368o
Abstract
This Communication reports the optimization of the first catalytic enantio- and diastereoselective hetero[4+2]/allylboration reaction to provide efficient access to α-hydroxyalkyl pyran derivatives. The key substrate 3-boronoacrolein pinacolate appears to be an exceptionally favorable heterodiene for use in Jacobsen's enantioselective reverse electron demand hetero[4+2] reaction with enol ethers, catalyzed by the tridentate (Schiff base)chromium complex 1. This one-pot three-component reaction was successfully applied to a concise total synthesis of (5R,6S)-6-acetoxy-5-hexadecanolide (2), the oviposition attractant pheromone of the female Culex mosquito capable of transmitting the West Nile virus.Keywords
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