Applications

Researchers from industries and universities have developed a wide variety of innovative applications using the diaza-Cope rearrangement with our mother diamine. These include tuning of chiral diamines in transition metal based catalysts and organocatalysts to make them more reactive or stereoselective.  Others have developed novel chiral diamine based porous materials, sensors, molecular levers, and therapeutic agents from the mother diamine. Some interesting examples are shown below.

Fu group at California Institute of Technology (USA) 'tuned' chiral diamine based Ni(II) complexes for Suzuki cross coupling reactions. Diaza-Cope rearrangement was used to make the diamines.


Zhe Lu , Ashraf Wilsily , and Gregory C. Fu JACS (2011) 8154

Nathan A. Owston and Gregory C. Fu  JACS (2010) 11908
Bunnai Saito and Gregory C. Fu JACS (2008) 6694

Carreira group at ETH (Switzerland) tuned chiral diamine based Ir(III) complexes for transfer hydrogenation reactions.

 


Omid Soltani , Martin A. Ariger and Erick M. Carreira OL (2009) 4196.


Hong group at Seoul National University (S. Korea) developed cyanide sensors based on novel chiral diamines that were synthesized from the 'mother diamine'.
 

Jae Han Lee, A Reum Jeong, Ik-Soo Shin, Hae-Jo Kim and Jong-In Hong OL (2010) 764.

Akine and Nabeshima groups at University of Tsukuba (Japan) developed molecular levers with a novel crown ether based chiral diamine that was made with the 'mother diamine'.
 

Shigehisa Akine, Sayaka Hotate , and Tatsuya Nabeshima JACS (2011) 13868.

James group at Queens University, Belfast (UK) developed porous crystalline materials from novel alkydiamines synthesized by diaza-Cope rearrangement.

 

Nicola Giri, Christine E. Davidson, Gavin Melaugh, Mario G. Del Popolo, James T. A. Jones, Tom Hasell, Andrew I. Cooper, Peter N. Horton, Michael B. Hursthoused and Stuart L. James Chemical Sciences (2012) 2153.

Cooper group at University of Liverpool (UK) developed microporous materials from chiral diamines made from the mother diamine.

 


Michael J. Bojdys, Michael E. Briggs, James T. A. Jones, Dave J. Adams, Samantha Y. Chong,

Marc Schmidtmann, and Andrew I. Cooper JACS (2011) 16566

Johnson group at University of North Carolina at Chapel Hill (USA) tuned transfer hydrogenation catalysts using the diaza-Cope rearrangement for a variety of reactions



Kimberly M. Steward , Michael T. Corbett , C. Guy Goodman , and Jeffrey S. Johnson JACS (2012) 20197.

Kimberly M. Steward, Emily C. Gentry, and Jeffrey S. Johnson  JACS (2012) 7329.

Chin group at University of Toronto (Canada) tuned chiral diamines as organocatalysts for stereoselective synthesis of Warfarin, a blood thinning agent.


 

Hyunwoo Kim, Cindy Yen, Philippa Preston, and Jik Chin OL (2006) 5239.


Busacca group at Boehringer Ingelheim (New Jersey, USA) developed Pd(II) complexes for stereoselective Heck reactions by tuning the chiral diamine based BIPI ligands using the Diaza-Cope reaction.


 

Carl A. Busacca, Teresa Bartholomeyzik, Sreedhar Cheekoori, Nelu Grinberg,

Heewon Lee, Shengli Ma, Anjan Saha, Sherry Shen, and Chris H. Senanayake JOC (2008) 9756.

Busacca, C. A.; Senanayake, C. H. Comprehensive Chirality (2012), 1, 167-216.

Ding group at Shanghai Institute of Organic Chemistry (China) developed monophosphine ligands based on the mother diamine. 

Jinzhu Zhang, Yang Li, Zheng Wang, and Kuiling Ding Angew. Chem. Int. Ed. (2011) 11743.

Liu, Yan; Sandoval, Christian A.; Yamaguchi, Yoshiki; Zhang, Xue; Wang, Zheng; Kato, Koichi; Ding, Kuiling JACS (2006) 14212.

Liu, Yan; Ding, Kuiling JACS (2005) 10488.


Gust group at University of Innsbruck (Austria) used diaza-Cope rearrangement to make a wide variety of diamines and their platinum complexes as analogs of anti-cancer agent cis-platin.

Maria Proetto, Wukun Liu, Adelheid Hagenbach, Ulrich Abram, Ronald Gust, Eur. J. Med. Chem. (2012) 168.