Work

Transfer of Chirality in the Rhodium‐Catalyzed Intramolecular [5+2] Cycloaddition of 3‐Acyloxy‐1,4‐enynes (ACEs) and Alkynes: Synthesis of Enantioenriched Bicyclo[5.3.0]decatrienes

Year: 2013

Type: article

Abstract: Chiral bicycles: Enantioenriched bicyclo[5.3.0]decatrienes were prepared from readily available chiral 3-acyloxy-1,4-enynes (ACEs) for the first time. In most cases, the chirality of the ACEs could be transferred to the bicyclic products with high efficiency. Inversion of the configuration was observed, thus confirming the predictions of previous computational studies.

Source: Angewandte Chemie International Edition

DOI: 10.1002/anie.201306919

Authors: Xing‐zhong Shu, Casi M. Schienebeck, Wangze Song, Ilia A. Guzei, Weiping Tang

Institution: University of Wisconsin–Madison

Language: English

Topic: Catalytic Alkyne Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funder: National Institute of General Medical Sciences

Award: Development of Cyclopropyl Metal Carbene Based Methods for Organic Synthesis