Synthesis 2016; 48(16): 2664-2670
DOI: 10.1055/s-0035-1562097
special topic
© Georg Thieme Verlag Stuttgart · New York

Enantioselective Synthesis of Planar-Chiral 1,n-Dioxa[n]paracyclophane-Based Phosphites and Their Application as Chiral Ligands

Takanori Shibata*
a  Department of Chemistry and Biochemistry, School of Advanced Science and Engineering, Waseda University, Shinjuku, Tokyo 169-8555, Japan   Email: tshibata@waseda.jp
b  JST, ACT-C, 4-1-8 Honcho, Kawaguchi, Saitama 332-0012, Japan
,
Miku Fukai
a  Department of Chemistry and Biochemistry, School of Advanced Science and Engineering, Waseda University, Shinjuku, Tokyo 169-8555, Japan   Email: tshibata@waseda.jp
,
Ryosuke Sekine
a  Department of Chemistry and Biochemistry, School of Advanced Science and Engineering, Waseda University, Shinjuku, Tokyo 169-8555, Japan   Email: tshibata@waseda.jp
,
Madhurima Hazra
a  Department of Chemistry and Biochemistry, School of Advanced Science and Engineering, Waseda University, Shinjuku, Tokyo 169-8555, Japan   Email: tshibata@waseda.jp
,
Kyalo Stephen Kanyiva
c  International Center for Science and Engineering Programs (ICSEP), Waseda University, 3-4-1 Okubo, Shinjuku, Tokyo 169-8555, Japan
› Author Affiliations
Further Information

Publication History

Received: 08 March 2016

Accepted after revision: 04 April 2016

Publication Date:
04 July 2016 (online)

Abstract

Various planar-chiral 1,n-dioxa[n]paracyclophanes possessing a phenolic hydroxyl group have been synthesized via enantioselective ortho-lithiation. Subsequent reaction with 2,2′-biarylene phosphorochloridites gave a new family of chiral phosphites. These phosphites were then used as chiral ligands in the enantioselective palladium-catalyzed allylic alkylation of dimethyl malonate with (E)-1,3-diphenylallyl acetate and the rhodium-catalyzed 1,4-addition of phenylboronic acid to cyclohex-2-enone.

Supporting Information

 
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