Enantioselective Synthesis of Bicarbocyclic Structures with an All-Carbon Quaternary Stereocenter Through Sequential Cross Metathesis and Intramolecular Rauhut-Currier Reaction

Authors

Yuan Qiao
Sanjeev Kumar
William Paul Malachowski, Bryn Mawr CollegeFollow

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.

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.

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