Tuning the peri effect for enantioselectivity: Asymmetric hydrogenation of unfunctionalized olefins with the BIPI ligands

Carl A. Busacca, Bo Qu, Nicole Grět, Keith R. Fandrick, Anjan K. Saha, Maurice Marsini, Diana Reeves, Nizar Haddad, Magnus Eriksson, Jiang Ping Wu, Nelu Grinberg, Heewon Lee, Zhibin Li, Bruce Lu, Dajun Chen, Yaping Hong, Shengli Ma, Chris H. Senanayake

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

The modular nature of the BIPI ligands allows for systematic optimization of each ligand region. The development of ligands optimized for asymmetric hydrogenation of the challenging unfunctionalized olefin substrate class is described. The naphthyl peri position, C-8, has been identified as a critical stereocontrol element in the design of these ligands. Highly enantioselective ligands suitable for hydrogenation of tri- and tetrasubstituted olefins are detailed.

Original languageEnglish (US)
Pages (from-to)1455-1463
Number of pages9
JournalAdvanced Synthesis and Catalysis
Volume355
Issue number8
DOIs
StatePublished - May 17 2013
Externally publishedYes

Fingerprint

Enantioselectivity
Alkenes
Olefins
Hydrogenation
Tuning
Ligands
Substrates

Keywords

  • asymmetric hydrogenation
  • BIPI ligands
  • naphthalenes
  • peri position
  • unfunctionalized olefins

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

Cite this

Busacca, C. A., Qu, B., Grět, N., Fandrick, K. R., Saha, A. K., Marsini, M., ... Senanayake, C. H. (2013). Tuning the peri effect for enantioselectivity: Asymmetric hydrogenation of unfunctionalized olefins with the BIPI ligands. Advanced Synthesis and Catalysis, 355(8), 1455-1463. https://doi.org/10.1002/adsc.201201104

Tuning the peri effect for enantioselectivity : Asymmetric hydrogenation of unfunctionalized olefins with the BIPI ligands. / Busacca, Carl A.; Qu, Bo; Grět, Nicole; Fandrick, Keith R.; Saha, Anjan K.; Marsini, Maurice; Reeves, Diana; Haddad, Nizar; Eriksson, Magnus; Wu, Jiang Ping; Grinberg, Nelu; Lee, Heewon; Li, Zhibin; Lu, Bruce; Chen, Dajun; Hong, Yaping; Ma, Shengli; Senanayake, Chris H.

In: Advanced Synthesis and Catalysis, Vol. 355, No. 8, 17.05.2013, p. 1455-1463.

Research output: Contribution to journalArticle

Busacca, CA, Qu, B, Grět, N, Fandrick, KR, Saha, AK, Marsini, M, Reeves, D, Haddad, N, Eriksson, M, Wu, JP, Grinberg, N, Lee, H, Li, Z, Lu, B, Chen, D, Hong, Y, Ma, S & Senanayake, CH 2013, 'Tuning the peri effect for enantioselectivity: Asymmetric hydrogenation of unfunctionalized olefins with the BIPI ligands', Advanced Synthesis and Catalysis, vol. 355, no. 8, pp. 1455-1463. https://doi.org/10.1002/adsc.201201104
Busacca, Carl A. ; Qu, Bo ; Grět, Nicole ; Fandrick, Keith R. ; Saha, Anjan K. ; Marsini, Maurice ; Reeves, Diana ; Haddad, Nizar ; Eriksson, Magnus ; Wu, Jiang Ping ; Grinberg, Nelu ; Lee, Heewon ; Li, Zhibin ; Lu, Bruce ; Chen, Dajun ; Hong, Yaping ; Ma, Shengli ; Senanayake, Chris H. / Tuning the peri effect for enantioselectivity : Asymmetric hydrogenation of unfunctionalized olefins with the BIPI ligands. In: Advanced Synthesis and Catalysis. 2013 ; Vol. 355, No. 8. pp. 1455-1463.
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