Catalytic Asymmetric Synthesis of 2, 6‐Disubstituted Cuneanes through Enantioselective Constitutional Isomerization of 1, 4‐Disubstituted Cubanes. Issue 37 (11th July 2022)

• Record Type: Journal Article
• Authors: Takebe, Hiyori; Matsubara, Seijiro
• Is Part Of: European journal of organic chemistry. Volume 2022:Issue 37(2022)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2022-07-11
• Subjects: Asymmetric synthesis -- Chiral scaffold -- Cubane -- Cuneane -- Pd-pincer; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.202200567
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: 2, 6‐Disubstituted cuneane has potential as a p ‐disubstituted benzene bioisostere and a novel chiral scaffold. It is a constitutional isomer of a 1, 4‐disubstituted cubane obtained via a metal‐catalyzed skeletal rearrangement. Unlike the highly symmetrical 1, 4‐disubstituted cubane, the isomerized 2, 6‐disubstituted cuneane is a chiral molecule possessing C 2 symmetry. Examining various chiral catalysts revealed that the Pd‐pincer catalyst provides a good asymmetric induction. Abstract : 2, 6‐Substituted cuneanes were obtained by metal‐catalyzed isomerization of 1, 4‐disubstituted cubanes and are stable cage‐like hexahedral compounds with C 2 v symmetry. In this process, the chiral cage‐like hexahedral hydrocarbon in one step. The asymmetric induction was performed using chiral P−C−P pincer Pd catalyst. The obtained cuneane will be a novel chiral scaffold.