Synthesis of 1,1-Spirobiindane-7,7-Disulfonic Acid and Disulfonimide: Application for Catalytic Asymmetric Aminalization

• Kurihara, Takumaru

• Satake, Shun

• Hatano, Manabu

• Ishihara, Kazuaki

• Yoshino, Tatsuhiko

• Matsunaga, Shigeki

Bibliographic Information

Other Title

• Synthesis of 1,1′‐Spirobiindane‐7,7′‐Disulfonic Acid and Disulfonimide: Application for Catalytic Asymmetric Aminalization

Abstract

1,1-Spirobiindane-7,7-disulfonic acid (SPISA) and 1,1-spirobiindane-7,7-disulfonimide were synthesized from 1,1-spirobiindane-7,7-diol (SPINOL) in 4 steps using a Pd-catalyzed Newman-Kwart rearrangement as a key step. These new catalysts possessing a rigid spirocyclic backbone were evaluated in a catalytic asymmetric aminalization reaction, and SPISA/iPr(2)NEt exhibited high enantioselectivity, demonstrating the utility of SPISA as a chiral BrOnsted acid catalyst.

Journal

• Chemistry-an asian journal

  Chemistry-an asian journal 13 (17), 2378-2381, 2018-09-04

  Wiley-Blackwell

Keywords

• 1-spirobiindane
• aminalization
• chiral BrOnsted acid
• disulfonic acid
• disulfonimide

Details

• CRID: 1050564289017086592
• NII Article ID: 120006716317
• DOI: 10.1002/asia.201800341
• ISSN: 1861471X
• ISSN: 18614728
• HANDLE: 2115/75353
• Web Site: https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fasia.201800341
• Web Site: http://api.wiley.com/onlinelibrary/chorus/v1/articles/10.1002%2Fasia.201800341
• Web Site: https://onlinelibrary.wiley.com/doi/pdf/10.1002/asia.201800341
• Text Lang: en
• Article Type: journal article
• Data Source:
  • IRDB
  • Crossref
  • CiNii Articles
  • KAKEN