Lowe Jason T, Panek James S
Department of Chemistry and Center for Chemical Methodology and Library Development, Metcalf Center for Science and Engineering, 590 Commonwealth Avenue, Boston University, Boston, Massachusetts 02215, USA.
Org Lett. 2005 Apr 14;7(8):1529-32. doi: 10.1021/ol0501875.
[reaction: see text] Development of new organosilane reagents bearing C-centered chirality where the stereocenter is fully substituted, and their use in the stereocontrolled synthesis of cis- and trans-dihydropyrans containing a trisubstituted olefin is described. The reagents participate in Lewis acid promoted [4+2]-annulations providing useful levels of selectivity with both aliphatic and aromatic aldehydes. A stereoselective synthesis of the C1a-C10 fragment of kendomycin (1) is also described.
[反应：见正文] 描述了具有完全取代的碳中心手性的新型有机硅烷试剂的开发，以及它们在立体控制合成含有三取代烯烃的顺式和反式二氢吡喃中的应用。这些试剂参与路易斯酸促进的[4+2]环化反应，对脂肪族和芳香族醛均提供了有用的选择性水平。还描述了肯多霉素（1）的C1a-C10片段的立体选择性合成。
