Synthesis 2020; 52(06): 853-860
DOI: 10.1055/s-0039-1690763
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Bis-BINOL Derivatives: Linking via the 3-, 4-, or 5-Position by Generation of Suitable C 1-Symmetric Precursors

Martha Kohlhaas
a   Institute of Organic Chemistry and Center for Nanointegration Duisburg-Essen (CENIDE), University of Duisburg-Essen, Universitätsstrasse 7, 45141 Essen, Germany   Email: jochen.niemeyer@uni-due.de
,
Fabian Lutz
a   Institute of Organic Chemistry and Center for Nanointegration Duisburg-Essen (CENIDE), University of Duisburg-Essen, Universitätsstrasse 7, 45141 Essen, Germany   Email: jochen.niemeyer@uni-due.de
,
Nirtharsan Paransothy
a   Institute of Organic Chemistry and Center for Nanointegration Duisburg-Essen (CENIDE), University of Duisburg-Essen, Universitätsstrasse 7, 45141 Essen, Germany   Email: jochen.niemeyer@uni-due.de
,
Frescilia Octa-Smolin
a   Institute of Organic Chemistry and Center for Nanointegration Duisburg-Essen (CENIDE), University of Duisburg-Essen, Universitätsstrasse 7, 45141 Essen, Germany   Email: jochen.niemeyer@uni-due.de
,
Christoph Wölper
b   Institute of Inorganic Chemistry, University of Duisburg-Essen, Universitätsstrasse 7, 45141 Essen, Germany
,
a   Institute of Organic Chemistry and Center for Nanointegration Duisburg-Essen (CENIDE), University of Duisburg-Essen, Universitätsstrasse 7, 45141 Essen, Germany   Email: jochen.niemeyer@uni-due.de
› Author Affiliations
Funding by the Fonds der Chemischen Industrie (Liebig-Fellowship Li 193/02 to J.N.) and Evonik Industries AG (PhD fellowship to M.K.) is gratefully acknowledged.
Further Information

Publication History

Received: 23 October 2019

Accepted after revision: 20 November 2019

Publication Date:
10 December 2019 (online)


In memory of Prof. Dieter Enders

Abstract

Bis-BINOL derivatives have proven highly useful in applications such as chemosensing or organocatalysis. In this account, we describe strategies for the linking of BINOL units via the 3-, 4-, or 5-positions, showing that unique synthetic strategies are necessary to address each position. We report the synthesis of suitable C 1-symmetric precursors, which are generated either by monohalogenation or by monodeprotection of C 2-symmetric starting materials, and their subsequent coupling to give linked bis-BINOL derivatives.

Supporting Information

 
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