Document Type
Article
Version
Postprint
Publication Title
Tetrahedron Letters
Volume
51
Publication Date
2010
Abstract
A new extension of the Birch-Cope sequence is described which allows the efficient enantioselective construction of highly functionalized, fused bicarbocyclic structures with an all-carbon quaternary stereo-center in two steps. The two-step sequence includes a cross metathesis between a terminal alkene and a polarized alkene followed by an intramolecular Rauhut-Currier reaction with a trialkylphosphine catalyst.
Publisher's Statement
(C) 2010 Elsevier Ltd. All rights reserved. The publisher's version can be found at http://www.sciencedirect.com/science/article/pii/S004040391000434X.
Citation
Qiao, Yuan, Sanjeev Kumar, and William P. Malachowski. "Enantioselective synthesis of bicarbocyclic structures with an all-carbon quaternary stereocenter through sequential cross metathesis and intramolecular Rauhut–Currier reaction." Tetrahedron Letters 51, no. 19 (2010): 2636-2638.
DOI
10.1016/j.tetlet.2010.03.026
Supplemental data
Comments
Supplemental data: General experimental details, copies of 1H and 13C NMR spectra, gas and liquid chromatographs and mass spectra for compounds 3a–d, 4a, 4c, 4d and 5. COSY and HMQC for 5.