Application of a CC Bond‐Forming Conjugate Addition Reaction in Asymmetric Dearomatization of β‐Naphthols1. Issue 33 (14th July 2015)

• Record Type: Journal Article
• Authors: Yang, Dongxu; Wang, Linqing; Kai, Ming; Li, Dan; Yao, Xiaojun; Wang, Rui
• Is Part Of: Angewandte Chemie international edition. Volume 54:Issue 33(2015)
• Page Start: 9523
• Page End: 9527
• Publication Date: 2015-07-14
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201503056
• Languages: English
• ISSNs: 1433-7851

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>A CC bond‐forming conjugate reaction was successfully applied to the enantioselective dearomatization of β‐naphthols. A C(sp2)C(sp3) bond is formed by using propargylic ketones as reactive partners. Good to excellent <italic>Z</italic>/<italic>E</italic> ratios and <italic>ee</italic> values were obtained by employing an in situ generated magnesium catalyst. Further transformations of the <italic>Z</italic>‐configured CC double bond in the products were achieved under mild reaction conditions. Moreover, the stereocontrolling element of this magnesium‐catalyzed dearomatization reaction was explored by computational chemistry.</p> </abstract>